Re: All is Strange in MS Land
I'll second the VirtualBox suggestion. Mine runs Vista so we can access our QuickBooks accounting software. On any reasonably up to date machine it's an easy install, and best of all if you change machines you don't need to re-install Windows and the apps - just copy over the directory.
In my experience the success of WINE depends entirely on there being someone knowledgeable who needed a specific app bad enough to keep at it until it actually worked reliably. The WINE database is full of entries that more or less say "THIS version works sometimes with THIS version of WINE, but not necessarily with YOUR hardware."
With notable exceptions like MS Office and popular games it's really a case of trial and error - try to install it and see if it works.