Beyond Compare: I have yet to find a better file/folder sync and poor man’s backup solution on Windows and nothing equivalent on Mac. Truly, it is beyond compare. I can’t do without it, so I run Beyond Compare on my Windows box and point it to a shared folder on the Mac whenever I have to do file or folder comparisons. UPDATE: Wikipedia’s comparison of file comparison tools is helpful.
Microsoft Money: I used to use Quicken. Quicken is fine for financial management, but their server software for connecting to banks and downloading transactions is significantly poorer than Money. The usual help from Quicken tech support was to delete an account and recreate it. Each time, I lost transactions older than about 90 days. Enough of that!