It seems like it would make sense to combine this with subuser to make sure you keep a known-good version of wine and its configuration. I've known wine compatibility to drift unpleasantly from time to time, or accidentally lost obscure config changes I made once...
(I have fond memories of a time when I could play Supreme Commander on linux in wine... but I've since lost that machine, and I haven't been able to reproduce the dang setup again since :( If subuser had existed back then, I'd probably have a snapshot and I'd be happily playing right now...)
Probably not.
Technically, wine was able to run various versions of Photoshop for years. But it was never stable nor complete enough to use it professionally, with wacom tablets and such.
