WINE has made tons of progress since CrossOver 8.0.0/WINE 1.0.16. Heck, I think they're up to version 1.0.32 now, if not 1.0.33. Most of the fixes are for 64-bit support, which is a good thingIn 10.7 have WINE working perfectly.
If Apple could put that off, I think that would make Microsoft be scared as hell.
To me the only advantage Windows has over OSX, Windows can run tons more applications.