Being a DM is challenging, mainly because of the broad factors you have to consider and the groundwork you need to lay. The gameplay doesn’t vary THAT much between player and DM, the DM just knows a little more and has to set up more ahead of time. It also takes a lot more acting and passion. The one big challenge is that the DM is often the arbitrator on mechanical questions; don’t be afraid to admit confusion and look it up, but when you make a call stick to it. It’s more important to be consistent than to be right, and it’s important to admit when you made a mistake and fix it.

World Design

The DM’s first challenge is building a world. This is challenging, and a full homebrew world isn’t for everybody. It’s perfectly fine to use an existing campaign setting, like The Forgotten Realms, with tons of existing information you can draw from. It’s just as good to take it and make it your own with some changes, to scavenge parts to add to your world, or to make your world from scratch. Either way, you should have it mostly pre-built, so there’s expectations in the world. If a king is supposed to be a terrifying dictator, the characters should Know that before they’re supposed to be terrified by him. Having information the characters should know accessible to the players is crucial, and giving them the chance to learn is as well. Obviously you cannot force a horse to drink, but you can give them insight via the talk of others. (Oh, you’re going to see the king? Watch your tongue or it might be cut out. To the left, you’ll see his cronies before you see him. Vs The king is that way.) They should be able to easily gain info on what countries are threats, the major players in the world their characters would know about, etc. Players never behave. No matter what you do, the plot you lay out won’t happen exactly as you thought it would. Crits happen both ways, players miss hints that are clearly laid for them, get their own goals or run away. If you want the plot to move a certain way, you have two options: Controlling them, or Guiding them. The first is often called Railroading, as the player feels stuck on tracks that they don’t get to direct. Most players really don’t like this. Forcing them to go one way, preventing them from picking their own path, or not letting things work in any but the way you set out is controlling them, and this is generally a bad plan. Giving them design cues to go a way (big shiny object, large scary thing the other way) or giving them the tools to handle something the way you designed (oh wow, you found a key? What does it go to) is guiding them. They may not choose to do it your way, but they now have the idea to do so, at least. Better yet, just let them do their own thing and let them find out how well it works, they’ll stumble upon the solution.

Players may sometimes just Not get it. This can often be prevented by good initial direction and expectation framing, but it doesn’t always work. Sometimes they forget, sometimes they may be lazy. Either way, it can be a frustrating experience watching them putter around in circles and frustrating for them to be stuck in a rut. However, caution against telling them outright! This just makes them feel dumb. Instead, be like a parent: leave out hints for them to find, but make it so they find them themselves. Give them something extra on a search check that wasn’t supposed to be there originally, but they don’t know that: they just think they found something. Have an NPC be a little loose-lipped: even if they weren’t supposed to know, there’s always the chance they overheard something. Have a minion or foe drop incriminating evidence, or a pickpocket run in the direction they’re supposed to go so they chase. This way they think they figured it out on their own, or at least figured it out. Nobody likes being spoon fed.

Just as players don’t always behave, the DM shouldn’t always either. It’s fun to trick players: have a good guy turn heel, or a treasure be a trap, or a potential success turn out to be a setback. There’s danger in this though; if players get tricked too much, they’ll stop caring. They won’t trust good guys, because they expect the heel turn. They won’t celebrate successes or enjoy treasure, because they expect them to go wrong. My rule is no more than 1 in 4 good things should have a catch, and no more than 1 in 10 should be a bad thing disguised as a good one. Even this is pushing it, unless your players show they really enjoy that.

As a DM, your job is to write a story, but one of the challenges is you don’t get to dictate every aspect of how it goes. You get to decide what the villains plans are, but it’s up to the players when and how they foil them. Because of this, you need to be careful about how you push the plot. Typically, you want important events to wait until an appropriate time, but unimportant villain progress should move independently of the PC’s. If everything happening revolves around them, the immersion in the world can be spoiled: the characters are the most important in the world, and that typically shouldn’t be your intention. However, the opposite is dangerous: if your antagonists push forwards completely independently, the players can feel hopeless and left behind. My rule of thumb is that One Big Thing happens per level, give or take. This may be an actual effort by the antagonists, or just an important discovery by the players: Perhaps at 3rd level the party learns of a plot by a bandit group, and embarks to stop it. This is the event: the bandits are making a plot. The bandits should then wait a bit, making progress but not executing the plot, until the party has made some progress so that it feels like a story beat, an obstacle. At 4th, the bandits attack the town, and the party faces them. The bandits shouldn’t attack before the party has had a chance to investigate and combat them, otherwise it feels like a failure to the players. Similarly, having them embark, battle, and discover the true bandit leader and embark on that quest all in one level is a bit rushed. They should have time to combat the bandits, attempt to foil them, learn and improve, before the next story beat lands. It’s hard to find the perfect balance, and there’s no cheat codes. Find what feels right.

Many DM’s worry about ripping things off. They feel some sort of embarrassment at borrowing ideas, or try to avoid it entirely in an effort to make a world of entirely original ideas. This is dangerous, for two reasons. 1- nothing is truly free of influence. Dungeons and Dragons grew from Lord of the Rings, which grew from reading Beowulf, which grew from earlier legends. No matter what you do, you’re borrowing from the things that taught you. 2- Other people have good ideas, and usually your ideas aren’t always going to be the best in the room. This isn’t to say you won’t have good ideas or ideas worth pursuing, but ruling out everybody else’s stuff is foolish, because in many cases you’re throwing away perfectly good content. Especially if the content you are influenced by (or that you’re outright stealing) is a game, film, or book, you are not just acceptably using it but furthering its intended purpose of entertaining people by bringing it to your gaming group. As long as you aren’t trying to make money off of it or garner praise from others by passing it off as yours and only yours, there is absolutely no harm in outright copy-pasting elements you like from other sources. In my world, you can easily see my sources for many things, and I’ll openly wear my influences on my sleeve. I encourage you to do the same. Take what you love and make it your own.

NPCs

As a DM, your main job is to fill the world with props, including people the players interact with. This is nothing different than designing a character to play, the objectives are just somewhat different. Rather than serving the role of an entertaining person to be, they should be an entertaining and/or useful person to be Around. Follow the same path in designing a player character to design an NPC, just consider what purpose they serve.

This first list consists of NPC’s you need in a game, barring particular exceptions.

• Villain: If your party wants to be protagonists, to have an objective, there has to be an antagonist. These can be any type of person, or even some vague entity or force, but the important part is that they are doing something, or trying to do something, that the players have an interest in stopping. A compelling villain has motives beyond “power” and “evil”, and should have redeeming traits and flaws like a player does. If you plan to have your villain combat the players, they should ideally be a combination of scary and cool, being able to do things that are fairly unique and dangerous. A story without any villains will be undirected, and require solely player investment and goals. Any less than total commitment will lead to it stagnating. Some tried and true villain archetypes:
  • Deep: This villain has motives that test faith. What they are trying to do has real reasons behind it, and even if the players have a good reason to oppose them, doing so should challenge them morally. This could be a priest trying to eliminate evil but going too far, or an escaped slave trying to take revenge on their masters. These villains should be played emotionally, and can lead to really memorable interactions.
  • Puzzling: These villains have unknown motives, and the players may not know who they are in general. What they are trying to do is hard to understand, and they may leave clues to lead to explanation. The players need to search and think to discover the truth. This could be a serial killer leaving mysterious crime scenes, or a powerful alien being causing unusual events. These villains should be planned out well ahead of time, and can lead to extremely exciting reveals when the players discover the truth. Puzzling villains can mix with both controllers and runners, where the puzzle is learning who’s in control or trying to trace the runner.
  • Hunter: This villain is the most simple kind, and often the most potent. A hunter villain is (at least initially) much more powerful than the players, and has an objective to destroy them or somebody the PC’s don’t want destroyed. In order to beat them, the party needs to survive or escape, and find a way to either incapacitate, kill, or otherwise eliminate the hunter. The hunter doesn’t have to necessarily chase the players, and could instead be a looming threat that has some foreboding deadline. This could be a persistent assassin, or a terrifying dragon. These villains terrify and should show their power, perhaps by killing a PC or an NPC, and can lead to an extremely gratifying victory when the PC’s finally beat them
  • Controller: This villain doesn’t battle directly, instead directing other, lesser antagonists from behind the scenes (or the figurehead, either works.) In order for this to work, the controller has to be smart enough and inaccessible enough that the PC’s can’t just take them out off the bat, and can be played for great dynamics as they attempt to outmaneuver the players. These can be the evil tyrant of a foreign nation, or a malevolent cult leader. These villains should be smart and have plans on plans, and can lead to a truly reviled character that can last a whole campaign
  • Runner: These villains are unusual, as rather than trying to combat the PC’s, they’d rather have nothing to do with them. This can be intentional or unintentional, but either way the villain has their own thing they’re doing and in order to stop them, the players have to catch them. This could be a killer who isn’t threatening the party directly, or a madman on the path of summoning a terrible thing from beyond. These villains should leave small trails forcing the players to think to chase them down, and can lead to a very potent desire in the player’s minds to catch them.
• Questgiver: In some sense, the players should have a character to give them a sense of direction, whether directly or indirectly. This can be as simple as paying them to do something, or somebody who faces a problem that leads the PC’s to the main plot. Without somebody to give them a quest, the players have to essentially stumble onto the plot and figure out what to do by themselves, which can happen but often doesn’t. A safe bet is some scholar to give them some foreboding lore, or a helpless person in need.
• Advisor: Players can get lost or confused, and an NPC to help put them on the right track is extremely valuable. This can easily be either the quest giver or the info guy, and the DM can do it out of game too. However, it helps immersion to have some wise or clever person the players know to subtly drop hints, and to help them when they get stuck. A story without this kind of aid can lead to players feeling totally out of options. A safe bet is a retired adventurer of some kind, or a friendly and world-weary innkeep.
• Informant: Excepting certain special games, the PC’s should rarely know every detail going into the adventure. Much of the adventure consists of learning things, and while much of this can come from old dusty tombs and runes in ruins, some should come from a person they can talk to, so the players can ask questions about things they want to know. This person can end up being an advisor, a questgiver, or perhaps even a villain! It can be a mysterious learned person they have sought out on a quest, or a sub-villain they’ve captured and are interrogating. No matter who it ends up being, it’s a good opportunity for the DM to feed the players info they missed by being brickheads (it happens a lot!). A story without these characters can leave the players feeling like they’re missing crucial info they can’t obtain.
• Authority: Whether or not the party needs to be kept in line, there ought to be a line to be kept. The region the party is in should have some sort of authority, with laws or guidelines. This tells the party when the people they are encountering are normal or abnormal, civilized or wild, law-abiding or criminals. There’s no right way to assign value to this, but if the party doesn’t know, they lose a lot of their frame of reference on how to judge people. A noble and righteous authority establishes the good and evil, and a villainous tyrant establishes the dangerous and safe havens.
• Shopkeep: The party can’t get everything they need from ancient holes in the ground (probably) and loot doesn’t serve much purpose just piling up in the corner. The party should have a place where they can trade out stuff they don’t want, and acquire stuff they do want, and they deserve a friendly (or at least, familiar) face in front of them to do so. Shopkeeps can develop a really interesting personality and ground the players in between adventures. A story without a shopkeep of some kind means the players get stuck with the things they have, and have less freedom to customize.
• Doctor: Regardless of whether the party has a healer, sometimes they get problems, physical or spiritual, that they can’t fix. Even if the doc isn’t easily accessible, the party should have an option: somebody who can remove a curse, or resurrect the dead. It may require a whole quest as payment! A story without some kind of doctor means that ailments can be permanent, or at least last a very long time, which means they are more scary.

The following category is types of NPCs not every game has to have, but they are fun to toss in to add flavor.*

• Minion: Sometimes, the guy you fight isn’t the bad guy, he just works for him. These are pretty necessary for controller-type villains, but not always. Minions should be similar to villains, but don’t follow the same archetypes: typically they are slimy sycophants, dumb brutes, or loyal allies. If the minion is smart and capable on their own, make sure they’ve got a reason to work for the villain! The minion reflects the villain if the villain isn’t there: a stupid minion implies an incompetent villain, and a big mean minion implies an even bigger, meaner boss.
• Hiree: The PC’s may not want to do certain boring, dirty, or risky work. In this case, they need a hiree: somebody who will do something for them. These types of characters rarely are stable. It’s one thing to seek glory in adventure, but it’s another thing entirely to seek a paycheck from those lunatics. They may have a particular useful skill, but their skillset shouldn’t really overshadow the players.
• Old Friend: These NPCs require player backstory and investment, but they can drive the story in a lot of interesting ways. These can be characters encountered a while ago, or somebody from a written backstory, but the gist is that they have an emotional connection with the players. Anything spoken through the mouth of this “old friend” is taken very seriously by players, as they associate their nostalgia for the game with the character. This can be used for good or for villainy, as they can nudge players in the right direction or make for a masterful backstabbing.
• Wizard: This character is pretty nebulous, and for good reason: they should be somebody who has far above the normal amount of control over reality. They don’t inherently have to be a wizard, and can be some other spellcaster or some otherworldly being. Either way, they can change things to suit them, and allow the rules of the game world to be bent a little bit. A powerful wizard allows for plot hooks like time travel, new worlds, etc that a standard person can’t really do. Plus, their immense knowledge and power can let them serve as several of the important npc roles, like advisor, information, or quest-giver. Any person this powerful should have a balance between brilliant and eccentric, and while they are very capable they should also have a distinctive (and odd!) personality that defines them
• Gray Ally: These characters may help the player’s goals along, but they are not inherently very good people (or at least, don’t align with the player’s moral code). This creates an interesting dynamic, as the players have to get along with them somewhat if they want their help. These characters work best when they ally out of necessity, rather than choice: the friction makes for interesting rp. This could even be a villain, forced to cooperate for the time being! Don’t over-use these characters, or the players will just learn to like them and the gray-ness gets ignored.
• Antihero: These can easily be blended with gray allies, but have an important distinction- where the gray ally is normally not good but is doing something for the party’s benefit, the antihero may be unaligned with the party whatsoever and does their good in an ambiguous way separately. This can serve as an interesting context to the storyline, where the party isn’t the only person trying to handle a situation, and the antihero serves as neither an ally nor a foe, just a third party. They can be converted into allies or enemies, or just kept as a piece on the board.
• Fanatic: Fanatic NPCs can rapidly change the course of a game, and should be used sparingly. A fanatic is any character that has a belief so potent that they will do it unwaveringly: these come as either Allies, Obstacles, or Shakers. Ally fanatics drive the players to do what the fanatic believes in, which typically will end up causing conflict and perhaps catch the players in a dilemma over what is the right thing to do. Obstacle fanatics simply refuse to bend for the PC’s, and have to be surmounted in some way. These can be villains, but honestly get a bit tiring if they’re just “EVIL EVIL EVIL”. Instead, a neutral-leaning fanatic that is just in the way, that challenges the players to adjust or get stuck. Shaker fanatics do just that, and shake things up. Their path won’t stop for anybody, and ideally whatever they’re planning to do makes serious waves. Fanatics with power can really do some serious things, and this makes them a compelling character archetype.
• Secondary Villain: Not every bad guy has to be on the same path, and some stories may involve multiple plots. Even more than that, one lesser villain can lead the players to the roots of the plot of a much more important or dangerous villain. A secondary villain should still be played much like a standard villain, but if they are functioning at the same time as the main villain, there should be a delineation in priorities between the two. This can be an evil person looking for the same artifact the party plans to use against the main villain, or somebody hoping to ride the chaos of the main villain to their own success. They could also be unconnected, but forming a hammer and anvil upon the party.

Adventure Design

There is no one secret to designing a good adventure, unfortunately. I can teach you to be a DM, but the difference between a good and great DM is the design of their adventure, and I’m truly not qualified to make somebody a great adventure designer. The only way is passion. Build what you love, and put love into what you build. The first step is that you HAVE to read modules. Every story is built on the shoulders of those that told it before you, and in order to get a feel for what stories work, how encounters should be balanced, pacing, etc you must get familiar with how other creators do it. In addition, these modules often have useful features: you can steal their maps to fill out with your own monsters, or steal their monsters to use in other battles. If you’re running short on ideas, it’s also not a bad idea to snip out a module or a chunk of it and use that in your story as well! Using the work of other creators to improve your own is a necessary step to becoming great.

There are a lot of monsters in D&D, and most of them behave differently and add different dynamics to a battle. I can’t cover them all, but there’s a couple categories I like to use to figure out how I want a battle to go. Using the right combos can turn a battle from mundane to deadly, and the wrong combo from challenging to pathetic. Think about your battles!

• Minion: These are bog-standard monsters, without extremes in either direction. They serve best in a batch to fill up the action economy along with other, stronger monsters. Examples are orcs, or bandits.
• Tank: These are monsters with a combo of high AC, large hp pools, and good DR/ hp regen. They typically aren’t super deadly (see Dragon) but they can take a lot of hits. These serve best as interceptors for DPS characters, forcing the party to maneuver around them. Examples are giants, or some undead.
• Thorny: These are a special variety of the tank role: they may not survive super long, but they’re harder to attack because they have some sort of retaliatory damage: when you attack them, you take damage as well. These are most effective against DPS characters with multiple attacks, and not very effective against most spellcasters. Examples are fiery enemies like the remorhaz, or acidic slimes.
• Assassin: These are the monster version of a DPS: they don’t have a ton of health, but they do a boatload of damage. This usually comes from a large number of attacks, high crit damage, or some additional health-sapping ability like poison or negative levels. These are most effective against lower-health characters, and should be paired with something to soak up damage or they die quickly. Examples are dire animals, or wights.
• Swarm: Swarm monsters are a specific problem: they don’t take physical damage normally, and demand AoE attacks of some kind to deal with. This can be a creature with the actual swarm subtype, or just a huge number of weaker creatures. You need to be careful with swarms, as parties without the appropriate damage output can very rapidly be totally overwhelmed and destroyed. These are most effective as sudden mass attacks, perhaps paired with a tank to give physical damage dealers something to do other than get eaten.
• Resistant: Resistant monsters just don’t take damage from a particular type. This usually pairs with another role, but adds an extra element of difficulty, as if they are resistant to a PC-used damage type, they are suddenly a whole lot tougher. These enemies need to be considered carefully: their challenge jumps dramatically, and the rest of their stats don’t suggest that. Examples are Golems, or oozes.
• Sniper: A variation on assassin: these enemies are not very dangerous up close, but can deal large amounts of damage from a distance. This often pairs very well with a high-mobility enemy, like a flier, allowing them to harass PC’s while constantly repositioning out of reach. These enemies pair well with tanks just like assassin, but are even better with swarms of a bunch of minions to limit player mobility. These can often mix with sniper, explosive, and changer in Wizard-type enemies, more later. Examples are spellcasters like a Beholder, or things with a breath weapon like a chimera.
• Control: Control enemies may or may not fit in another monster role, but they all share the ability to do mass debuffs or other forms of preventing players from executing their gameplan properly. These enemies are really dangerous if they prevent a part of the gameplan that’s required to stop a resistant creature, like preventing casters from casting against a physical-damage resistant monster. These can often mix with sniper, explosive, and changer in Wizard-type enemies, more later. Examples include things with an aura of fear like many undead, or things that can freely cast wall spells like many fiends.
• Explosive: Explosive enemies are an empowered sniper enemy usually, as they can deal AoE damage, confirming damage to a whole group. Some instead explode when they die, making killing them very risky. These enemies pair very well with tanks resistant to their damage type, like a fire giant for a monster shooting fireballs. These can often mix with sniper, control, and changer in Wizard-type enemies, more later. Examples are things with wide range breath weapons like a Pyrohydra, or something explosive like a demon.
• Healer: These are fairly simple: they heal their allies. This type of enemy doubles up the effectiveness of a tank, makes assassins more durable and able to deal more damage over time, etc. These are extremely dangerous with resistant enemies, as it makes the existing difficulty of dealing damage to them much more problematic. They are fairly effective in any group that can keep the healer safe from attack. Not many monsters are healers inherently, but some have druid or cleric casting like a dryad or a fiend.
• Death Ray: Death ray enemies typically don’t have a large pool of hp or super dangerous attacks, but have a particular thing going for them that lets them instakill people. This is often a death gaze, some kind of petrification, etc. Death ray enemies are obviously dangerous, and serve best when they’re hard to get rid of, letting their problem activate a number of times. Some more powerful enemies fit a lot of roles and also have instakill abilities, we’ll talk about those in wizard. Examples are Basilisks, or medusae.
• Changer: Changer enemies provide some sort of unusual alteration to the battlefield, that forces battles to progress along new paths. They can make other monsters harder to hit, make players less effective, etc. These serve best with already-dangerous foes, as the changer itself is typically a one-note problem to fight solo. These can often mix with sniper, explosive, and control in Wizard-type enemies, more later. Examples include ethereal/incorporeal foes, burrowing foes, or monsters like the gravorg that alter gravity or some other battlefield feature.
• Wizard: When you mix the ability to change the battlefield, damage from range, and controlling enemies, you get a Wizard! These don’t have to be actual wizards, they can be any spellcaster or just particularly magic monsters. Wizard enemies are extremely potent and dangerous, mainly because of their wide array of options. Wizard enemies are good bosses, and they pair very nicely with tank enemies to keep players from getting to the wizard. Examples include actual evil wizards, liches, or powerful outsiders like demons.
• Dragon: What do you get when you take a spellcaster, a tank, innate debuffs, high damage potential, and good mobility? You get a dragon. Dragons are half of the name of the game, and at least in 3.5 are the most intimidating and dangerous foes by far. Using a dragon means you want to really test the party, because there is very little they don’t excel at. The one example is healing, as the only way to kill a dragon is to weather the storm until you can wear them down. Adding a dedicated healer makes a dragon into a nearly impossible foe, so be careful. Some potent monsters mimic a dragon-type, like a balor or pit fiend with teleportation, high hp and damage, and spellcasting, and you can consider them similarly.

One of the challenges in adventure design is keeping things at an appropriate difficulty level. Too weak, and the party doesn’t feel like they’re accomplishing anything. Too hard, and you end up with a TPK. There’s a LOT that influences balance, and I absolutely cannot explain it all to you. There are two huge things to consider in 3.5: Quality beats quantity, and something a couple levels high can waffle-stomp a group. Secondly: you can PULL PUNCHES! If a fight is going bad, have some deus ex machina help them, or fudge a little bit. You’re the DM, it’s the only time that’s ok. Never fudge to make something harder, but fudging to save your players is ok. This shouldn’t be a common thing, only when you fuck up balance.

A key element in adventures is the player’s ability to survive it and get out with something shiny at the end. If the whole thing feels like a grind, or feels pointless because they’re not getting rewarded, they won’t want to do it. In order to make adventures fun, there need to be periodic breaks to recuperate and recover, to plan. Similarly, there needs to be motivation at the end. Usually this is saving the world and sweet sweet money, but there’s a number of other things you can use. A great option is a powerful magic item: who doesn’t love a cool sword. Be careful with these, as they do affect your player’s combat power. Plus, after a while they don’t really need new cool swords, they’ve already got some. Some better solutions for unique rewards:

• Land and titles! Cool house, now they’re a Lord!
• Favors from powerful beings!
• Access to rare and unique knowledge, like new spells!
• Friends/allies who will follow them around!
• A Boat!
• Rare and useful materials, like spices!
• Art and Literature!

Give out unique things at the end of adventures, and players will look forward to it!

At the start of an adventure you want to know what you’re getting into. The typical structure is:

1. Hook-> Find out about a problem
2. Look-> Learn about problem
3. Go-> Travel to source of problem
4. Fight-> Battle an obstacle in the path of solving the problem
5. Recuperate-> A story beat for them before proceeding. Repeat 2-3-4-5 as necessary
6. Final Boss-> Battle the source of the problem, usually some evil wizard or similar

In order to make this structure work, you need 3 things: A problem, a person causing the problem, and an obstacle the party has to overcome before fighting them. Without a problem, it’s just murder. Without a person to battle, it’s a little undirected. Without an obstacle, it’s very short and unfulfilling. In addition, it’s very helpful to have an interesting backdrop for the story (the lava-bathed lair of an ancient dragon whose bones litter the halls is WAY more fun than Nondescript Cave #5, even if it has nothing to do with the villain), and a decent hook to get the party motivated (‘there’s this bad guy go get him’ is boring, but ‘your long estranged father is attempting to resurrect your dead mother and destroy your home city’ is FUNKY). However, the players won’t always play along! As we discussed earlier, they may go the wrong way and you might need to get them on track. It is a much more positive game experience if the “wrong way” also is fleshed out somewhat keeping their immersion, and even better if you plan ahead for potential mistakes and find a way to tie them back to the main story! However, be ready to voice a random dwarf named frantically opens fantasynamegenerators.com Timbert because the party decided that talking to him was the plan. Sites like Fantasy Name Generators or donjon.bin.sh are a fantastic tool to have in the back pocket.

As a DM, it’s ok to let something cool fly even though it doesn’t quite fit RAW. However, it’s incredibly important to keep your answers consistent for all players. If you let Zipper jump across the moving vehicles, you need to let Tarok do it too. Similarly, if you make a rule change for your own NPCs, the same rule change should go for the PCs! Finally, if you make a ruling on a non-RAW issue, you should do your best to stick with whatever your ruling is later. It’s very frustrating for a player if the DM can’t provide a consistent set of rules to work with.

Every player and DM likes games a little differently. Some players like silly games, or easy games, and some like serious and difficult ones. Some players like 12-hour marathon sessions once a month, some like 2 hour sessions every week. There is no right answer! You need to talk to your players and find what works best for you and your group. It is a game, find what makes everybody happy.