Couldn't tell ya... only thing I've ever tried to get running with it was Altium, I failed and gave up on that... More than likely not Wine's fault, dumbass me just can't figure the magic settings and commands to make it work with Altium.

Depends 100% on the application and the only way to know, is to try. For instance, Adobe Acrobat doesn't work (I occasionally need to edit PDFs and know that program the best since it's the one I used for nearly 2 decades), a few different trading apps work (Oanda, ThinkorSwim), and some Really weird stuff absolutely doesn't (IC programmer). Simple games seem to work fine, haven't tried more intensive ones as that's not my thing.

The more time you spend in linux though, the more you find yourself finding alternatives that are native to linix and learning them.