Thought I’d create a distinct thread from the previous one asking about daily use, because I really do want to hear more on people’s pain points. Great to know people are generally sounding pretty positive in those posts who recently switched, but want to know your difficulties as well! This way old and new users can share their thoughts, hopefully to inspire a respectful discussion.

A pain point from a beginner perspective is when you need to install multiple apps under the same prefix for them to communicate with each other, and then you need to have environment variables telling apps the path of your prefix. It is all very archaic in feel and still a very confusing, manual, and error prone process.
The UIs for Wine and WineTricks are so barebones and primitive - they barely help.
When you say multiple apps under the same prefix, would that be specific to Wine (or could you give another example).
I did not know prefixes had any context other than Wine. Anyway, see my other reply for context.
Do you have an example? I haven’t used wine for very much (except steam under the hood, lol), but I’ve never had apps need to communicate in any way I think
I’ve been doing some Archipelago games recently (archipelago.gg) and some of them require the game to be installed in the same wine prefix as the Archipelago client. For these games to be properly integrated with Archipelago they often need mods or servers which function as separate applications but need to hook into the memory of the running program.
Sometimes this requires a bunch of complex export scripts and cli commands to get the programs talking to each other. On Windows you can install the game and mods and it will just work - this is obviously not the case with Wine.
Ooh that’s cool, makes sense that those would need deeper integrations