When will Wine be good enough for the average person to use? One test is, "Is it good enough to let your spouse migrate to Linux from Windows?". My wife's must-have app list is roughly
Microsoft Office '97 Adobe Photoshop Elements 1 Ulead PhotoImpact Macromedia Dreamweaver 8 Musicmatch Jukebox 8 FamilyTreeMaker 2006
And you know what? All of those basically work except for Photoshop Elements. They need some cosmetic work, and a native DLL or two, and probably a few obscure bugfixes, but I think that's it. (I didn't test Office '97, since I expect she'll be using Crossover for that, as Codeweavers tests that app pretty well.)
It's possible that by this time next year Wine will pass this test for me. - Dan