wine seems broken. I tried to start some windows 98 applications (e.g., notepad). It will write some font related messages to the terminal and then hang. Killing the process and restarting it the xfs will crash.
Just testet at home with win2k and it works!?
I don't have any stock Windows applications, but the wine package in Roswell worked pretty well for all sorts of freely downloadable stuff (we tested it on some of the "most popular downloads" from winfiles.com).