I have found that Ubuntu (and Debian for that matter) work very well if you use the package managers like you should.
WINE also works quite well and has an extensive list of fixes and documents for how to get specific software working. For example, I installed Office 07 (very easy to do) and PowerPoint didn't work. All I had to do was use WINE Tools and check one box and PowerPoint worked flawlessly.
The truth (imo) is, if you have the patience for it, Linux is a great alternative to Windows. Really, the only thing Windows has over Linux is its gaming support. My two cents.