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I've been playing TTRPGs regularly for about 9 years. About 2 years of Pathfinder 1e (including a total conversion mod for Interface Zero, when that was in beta), 7 years of D&D 5e, with a few sessions each of the Avatar The Last Airbender - Powered By The Apocalypse, Pathfinder 2e, and a small spattering of OSR one-shots.
I actually don't have any major problems with D&D 5e. It does some things pretty well, it is serviceable for the play style that my group has, and the combat tactics and strategy are enjoyable for what they aim to be. I forsee my group playing 5e for a long time to come. So when I list my problems below, note that these are not dealbreakers, and indeed some of the "problems" are things I only want to "solve" for some games and dont necessarily need to completely eliminate them from my TTRPG life.

Which at times includes long-time players I have played with in multiple games. These are smart people (including artists and engineers) but who dont have the brainworms that makes them want to build an encyclopedic knowledge of feats and subclasses. Understanding complex rules requires a specific type of procedural thinking, and the promise of TTRPGs (creativity, freedom of choice, etc) should not inherently depend on having a strong procedural mindset. (I can explain my thoughts in more depth in a future post, if people are interested, just let me know.)
No individual rule in 5e is especially complicated on its own, but I have had to explain the rules for grappling probably close to 100 times after 7 years of playing 5e.
Now, I actually do not care about my TTRPGs being especially balanced between characters. I do want all players to be able to meaningfully participate, but I think a well-designed TTRPG can allow characters that are multiple levels apart to still participate meaningfully (if unevenly). Instead, this point is to talk about the challenge in managing game difficulty.
5e player characters are strong, and more importantly, they are very resiliant after a certain level. This isn't necessarily a big deal - you can just pump up the power of monsters and traps - but it does have rippling effects on the game design. For example:
Including open tables, sandboxes, a wargame overlay* and/or domain play, etc. I want to allow for guest players, newbies, players asynchronously controlling villainous factions, etc. I want to be resilient to a player bailing on a session. I want to scratch the itch of my player who is obsessed with alchemy, my player who wants to play "small business simulator", and my player who just wants to play a murdergoblin, seamlessly. And I want to scratch my own itch: I want to manage a castle and domain. And I want to be able to include players' cousins, acquaintances, and coworkers to play whenever they come to town.
I want to be able to pick up and play with limited prep, using procedures or easy-to-improvise content. I want to be hanging out at the pool, and when the sun sets and we ask "What do we want to do now?", one answer can be "lets play an rpg" without worrying about whether I'm prepped. I want it to be viable - even easy - for multiple people to DM in the same campaign.
Much of the above is difficult with 5e, due to the amount of time it takes to create characters, the complexity of their mechanics, and the powerlevel difference between characters even a few levels apart. If all players were cool obsessed nerds like myself, those issues would be less prevalent - some players roll up new 5e characters just for fun! And for some DMs, generating procedural content is ezpz! - but if I want to play with a broader social network, I need it to be as seamless as unpacking a boardgame.
*I mean, traditional wargames, not minis wargames, although the latter could be fun to resolve mass combats

Stay tuned for part 2: Experiments