I asked my wife what apps she uses daily on Windows, and tested all eight with wine from cvs this weekend. Results: 2 of the eight actually installed and ran properly. She was duly impressed - she thought it was going to be zero.
Apps that Work: Macromedia Fireworks (2002) Font Xplorer Lite
Apps that install but don't run: Macromedia Dreamweaver (2002)
Can't install: Microsoft Office '97 Adobe Photoshop Elements Ulead Photoimpact Musicmatch Jukebox FamilyTreeMaker 6
I filed bugzilla reports for all the problems I found. Links at http://kegel.com/wine/qa/#app.home - Dan