Challenge Accepted: Meta challenges

I just can’t stand being told I’m a horrible person too many times in a single day.
As long as we’re talking about challenge, we have to also talk about the things which create more challenge that aren’t a function of any part of game design. They’re not elements of poor design, they’re not fake difficulty, they don’t fall under the header of things that appear to be challenges but really aren’t. Yet they’re still challenging, and they can still knock you flat on your rear just as surely as a genuinely challenging bit of content will.
This is a collection of what I call meta challenges, challenges that are very much there but also have little to nothing to do with the actual challenge level of the game. None of them are coded into the game, but all of them are elements that make playthroughs more difficult, often stalling players entirely despite the fact that they’re obviously not a part of the core experience. Some of them brush up against fake difficulty in a few places, but all of them are still distinct from it by not providing a challenge to every player, just some players.
At its most basic level, all roleplaying is a form of wish fulfillment. Sure, you may not want to be your characters, but you presumably enjoy slipping into their heads for a little while. It’s a chance to step out of yourself and engage in behavior you never would in a normal setting, whether that behavior is something you’d personally find reprehensible or just something different from the norm. (Slaying monsters, for example, does not form the foundation of a solid career path in modern society. I’ve checked.)