i recommend running wine and winex side-by-side and see which programs work with which. even though wine is supposed to work with apps better and winex with games, i've used some apps that only work in winex. use script's from this guy's web site to install them:
that'll get you the most current source of wine and winex straight from cvs, compile it, and install it for you. it's a beautiful thing. if you are really intent on getting rid of windoze, you might consider commercial wine such as purchasing Transgaming's WineX or Codeweavers' Crossover products.