If you're looking at possibly spending a couple hundred anyway, have you thought about getting an archival program? Some HD's come with them, as I think the 250GB drive we have does.

Also, back to backing up programs, while that's a fairly simple matter on the Mac OS, it's a lot trickier with Windows. Some programs install bits and pieces of themselves into the OS itself (Registry), and you can't backup all of Windows with Stuffit. At least not as far as I am aware.