Will my iPod work on the latest iTunes version?

Some years ago (circa 2009) I've updated my iTunes to a latest version and it wouldn't let my classic iPod (it's latest software version is version 1.1.2 PC and I'm currently using Windows XP)sync - it'd tell me to restore my iPod, and when I did it would tell me there was an error and my iPod couldn't be restored. The only fix I (and lots of people) found to this matter was to downgrade my iTunes version to vs. 7.6.2.9, and my problem was solved.
However, this past week Apple decided to put a giant ad telling me to upgrade my iTunes to vs. 10, and doesn't let me see the songs I have on my library and consequently does not let me pass them to my iPod, since it's not synced with the software.
So, I'm left with two simple questions:
1) If I upgrade my iTunes, will my 2007/8 classic iPod work or will I have the same error again? And if I'm stuck with this same problem:
2) Is there any way I can keep using my good old iTunes version? What can I do to keep my iPod working?
Thanks in advance for the help!

Are you still back at SP2 for your XP or have you updated to SP3, Bianca?
(The symptoms you're describing are consistent with a Windows drive letter confusion. The hotfix addressing that issue on XP was rolled up into Service pack 3. So if you're up at SP3 now and you were getting a drive letter confusion back then, you shouldn't have that trouble again now.)

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http://support.apple.com/kb/HT1926
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http://support.apple.com/kb/TS1369
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