Honestly this probably used to be more true, and maybe still is if you use a weird distro, but if you go for the popular distros most of the time the solution is a few terminal commands that can easily be found by searching.

Unfortunately, yes, running windows apps on wine is sometimes unreliable, not all of them work, some work ok, and some work well. But I mean, you’re trying to trick windows apps into thinking linux is windows, there’s bound to be some hiccups, the fact it’s even possible to the extent it is without a multi billion dollar corporation backing development is already pretty impressive. There may not be any help available if nobody has taken the time to get it working simply because the company isn’t going to tell you how to run their software in wine, microsoft sure as shit wouldn’t help, and the wine devs can’t possibly be expected to know every little bug in possibly niche closed source enterprise software and offer a solution. Basically “you’re trying to do weird shit, and unless someone else has tried that same weird shit and posted a how to, nobody knows, it’s possible you’re the first to even try. Maybe ask on stackoverflow.”

Ime the real issue is that people don’t want to learn a new system even when they’re upset with their current one. Just try to get someone who complains about X or Y on android or apple to switch, it’s not hard to learn the new UI but nobody wants to.