Thanks for your reply.
While I agree that i'm running a pretty old version, as I mentioned in the original post, I did indeed try downloading a trial version of the newest release of MC14, and my ipod was not detected there. If I can get MC14 to work, I would purchase an upgrade, but if I'm going to have the same problems, and I haven't seen any other compelling reason to upgrade (not that MC14 doesn't have enhancements, just none that fit my needs).
My personal guess is this is more of a 64bit issue than either a win7 or MC issue, but I'm noticing a few others are having the same issue...i'd love to get this resolved for everyone.
I ended up wiping my IPod classic, and did a restore to factory first thing this morning. I'll report back later on whether that helped or not...I hope so, as I'm missing my tunes.