As it turns out, having to reinstall windows is a (relatively) painless way of updating the applications that you use... and trashing the ones you don't. Still would not recommend it as a fun time activity, though.
And for those people who say that you don't really need a CD copy of the software, because hey, you can just download it, right? -- just about everything went right back in *except* the one that was acquired via streaming download. I'll probably end up buying it again. (It's Quicken, whose idea of customer service leaves a lot to be desired.) So, yeah. You need the CD.