We've come a long way in the last 2 years. We're at a point where MOST Windows software works flawlessly. I said "pretty well" as theres no doubt a few that don't and it'd be a bit disingenuous for me to suggest otherwise.

I certainly wouldn't come into this with knowledge on wine older than 2 years and make a snap decision though as its a totally different landscape - no weird quirkiness and tweaking needed for the vast majority of applications anymore.