DM overload at higher levels

I won’t reiterate the website’s functionality issues; Dadi from Mistic Arts summarized them eloquently. I hope those concerns are being addressed, and I strongly encourage updating the infrastructure before adding new features.

My primary concern is a deeper structural problem in the current iterations of Dungeons & Dragons: the core system begins to break down in Tier 2 and Tier 3 play, just as players become most invested in their characters.

Some of these problems involve monster statistics, but others concern player abilities, hit-point recovery, and the relationship between the rules and the world they represent. A Strength 16 gnome should not necessarily be equivalent to a Strength 16 goliath in every meaningful context. A paladin can use Divine Smite virtually without limit because the primary constraint is simply taking a long rest. Rogues, in particular, can consistently undermine encounter design. When damage has little lasting consequence and a near-death experience can be erased by a nap, combat loses much of its tension. There is also little incentive to develop finesse, negotiate, or talk one’s way out of danger when the rules make direct confrontation so easy and recoverable.

At higher levels, standard monsters are often defeated by basic player abilities, leaving DMs with an unsustainable choice: run encounters that are effortless or flood the battlefield with enemies. When players must wait through 20 enemy turns before taking their own, combat becomes a tedious slog rather than an exciting part of the game. The underlying issue is a severe disparity in action economy between a party and a single boss, which DMs are often forced to compensate for by inflating hit points, adding monsters, or extensively homebrewing stat blocks.

DMs should not have to redesign the products they purchase simply to make them playable. These changes can also damage narrative consistency. When familiar creatures suddenly receive unearned legendary abilities or drastically altered statistics, players notice that the rules are being rewritten around them, undermining immersion and trust in the game world.

D&D has evolved beyond a game about narrow dungeon corridors into one centered on rich, diverse worlds. Its action economy, recovery systems, and character design need to evolve as well. The game’s long-term success depends on the people who run it. I took a 35 year gap in playing. I had to become DM to introduce my kids to the game. It has been great but now, at Level 8, it is wearing me out and I feel the same from my players. I am afraid the only fix is to scrape the game and restart with new characters at level 1. Though without the characters they have built, I doubt they will want to start again. Their lives are busy.

In order:

The team has been talking about the backend rebuild for months. It's already in progress and we've been hearing exciting things about it for a while.

16 strength is 16 strength. There's no reason to believe a gnome that does enough reps can't be as strong as a goliath. Insisting on innate reasons they can never be equal just reproduces gross real-world misconceptions into what's supposed to be a fun game.

A long rest is a huge constraint if you're DMing creatively. Sleep getting interrupted by danger as a story trope predates written language. If you want to increase difficulty and tension and limit the ability to heal and recharge abilities, why on earth would you ever let the party finish a long rest anywhere but in the safety of a city or castle? Also the 2014 Dungeon Master's Guide has a great section on variant rules for healing and resting that make it very easy to dial up or down difficulty and tension.

As a DM who ran a mini campaign inspired by My Cousin Vinny that ended up having zero combat, I promise you it's possible to create encounters based on the social and exploration pillars that players will feel engaged in and want to talk or puzzle their way through rather than just bashing heads. When creativity is allowed to flourish this game can easily be a lot more than just combat.

"Either one pushover enemy or a flood of enemies" is a false dichotomy. A small group of enemies with complementary abilities running crowd control on the party works great. There's such a variety of choices between just using one enemy and flooding the zone, and all it takes is a little creativity to find those sweet spots. And that's before we get into the joys of homebrewing monsters.

Which segues nicely into the fact that DMs tinkering and redesigning things has been a feature not a bug since the very beginning of D&D. And there's a long history of DMs doing that tinkering to overcome the problem of players using meta knowledge of the game to cheese their way through fights - things like knowing monsters' hit points, abilities, resistances, etc. - by turning those expectations on their heads. And that's a good thing. A high fantasy adventure world is one of wonder and surprise. Encountering monsters that don't fit expected molds enhances that immersion. Homebrewing is a great outlet for creativity that keeps things fresh and exciting for DMs and for players.

I'm being extremely unsubtle with the running theme of creativity here because it's so important to the game. If all you're doing with your campaign is using the rules as definitions and boundaries of your play experience, you're missing more than half the game. You're painting by numbers when you should be listening to Bob Ross. He had some great segments where he would tell viewers things like "this is your world and you have such amazing power to do anything you want with it." That's the essence of DMing. Mix things up. Move them around.

I am at the point where I have run multiple campaigns to and beyond level 20.  I strongly disagree with the idea that the core system breaks down at those levels. In fact, I would argue those levels are where the game really begins to sing, provided one utilizes the system to its fullest potential. 

That is not to say there are not problems with high level gameplay, merely that the problems are not “structural.”  These problems can be divided into three general categories: (1) lack of official support from Wizards, (2) DMs inexperienced at running high level content, (3) player problems

Starting with the first point, Wizards, under their old leadership, woefully neglected high level play.  The previous game designers, Crawford and Perkins, admitted that.  And they admitted their reason for doing so was self fulfilling - campaigns often fizzle out at high levels, so they focused on the low… meaning they did not produce enough high level content resulting in campaigns running out of fun new things and thus fizzling out.

Moreover, Crawford and Perkins were bad at monster design. Unacceptably so.  Even the very limited number of high level monsters they released were drastically underpowered and lacked the interesting set of abilities required to match high level characters and keep from being stale.

Finally, due to this lack of content, there’s very little official guidance on how to DM at higher levels, which requires far more advanced skill than low levels.  I think the designers wrongfully believed that DMs would figure things out by the time they hit high level play, which five decades of gameplay has shown not to be the case.  This failing has exacerbated the DM issues below by not providing official guidance. 

Moving on to DM problems, the most notable problem is not sufficiently challenging players.  There are several ways to do this. 

Rests should be few and far between.  You do not simply “take a nap” and heal - you have to spend a full hour resting, without any interruption.  In a properly dangerous environment, that is going to be difficult. However, many DMs are overly permissive with their rests, and that overly permissive nature only gets more damning to a campaign the higher level players are. 

Second, DMs need to tax player resources constantly.  Even trash fights should be deadly enough to require players spend spell slots or other abilities, rather than just whittling them down before moving to the next encounter.  Puzzles and traps should put pressure on players even when they’re out of combat. Social or investigatory encounters should encourage creative use of abilities and spells.

Third, combats need to be more than just tank and spanks. Dynamic monsters that keep players on their toes.  A lot of adds (highly recommend Flee Mortals! for minion rules).  Puzzles and alternative objectives that need to be done in combat.  Players at that level can do a lot of cool things - the DM needs to make combat equally interesting from their side.

Fourth, the combat narrative breaks down.  Lots of folks complain that high level characters feel like “superheroes” who no longer fit into the world.  This is a worldbuilding failure that colors how combat feels.  Consider that, in every official world, there are powerful folks like Mordenkainen (many of whom started as player characters of game designers).  So, while the party may be special, they are not unique, and thus feel more like an organic part of the world in their exploits.

Lastly, at least for this short list, DMs fear killing players or major NPCs.  If players do not feel reasonably at risk of dying or losing folks important to them, all of these other points are exacerbated.  They’re less likely to use resources judiciously, saving them only for boss fights they can then steamroll.  More likely to take rests, since delays do not mean friends dying.  Less likely to be engaged in combat, since the outcome is decided.  High level games can work in low-death, more causal settings… but they do not shine in that kind of setting.

One last category is player problems.  Players have a lot to track at that level and need to be prepared for their turns.  Slow players are one of the worst aspects of high level play, since they ruin the pacing for the rest of the table.  Likewise, if the DM is running a proper high level game, content should require players to pay attention to a dangerous and evolving scene - if you have players who do not do this, the content breaks down. 

So, what can a DM do to fix this?  

Third party content often contains content unbalanced against official content.  Bad for player facing options… great for DM options.  Since official monsters are underpowered, overpowered third party content is generally more level appropriate, and many of the designs are far more interesting than what Wizards produced under the old design team they’re transitioning away from.

Homerules to make combat track how you play.  I am personally employing Dadi’s rest rules, which are a happy medium between the official regular and hardcore rest rules, both of which I feel are flawed (though, if I had to play official rules, I’d go with the more dangerous rest rules).  I am also fond of Critical Role’s rules making resurrection magic have a failure chance that increases with each subsequent death, as that adds actual consequences to dying.

Work on making combat more interesting.  There’s lots of solid videos on this is one looks around. 

And acknowledge some groups just are not going to like high level play, particularly if players are younger or have attention span issues.  The system might be able to work well when played in the right hands, but that doesn’t mean it is for everyone. 

" I took a 35 year gap in playing"

This is the real issue.  35 years puts you in likely 2nd edition AD&D, right?  Yes the game is much different now, reflecting more modern philosophies (not all of which I agree with) but you will get it if you keep at it. 

While there are problems with high level gameplay, none of the things the OP points out are among them. The big issues are

1. The number of available PC options explode, making it very hard for players to remember everything they can do, and for the DM to have an adequate understanding of the PCs capabilities so they can create challenges that actually feel challenging, rather than trivial or impossible. This is particularly a problem with classes such as wizards.
2. Related to this, tracking of resources and status effects is increasingly difficult.
3. Balancing tools become increasingly unreliable as PC capabilities diverge. Published tools basically don't work at all.
4. There are a decent number of flat broken abilities (mostly higher level spells) that you have to ban or incorporate specific countermeasures.