Synching problem with 2nd gen Shuffle

I've had a 2nd gen iPod Shuffle for several years and have always had it work well. But recently it has trouble synching when I plug it in. Whether using Autofill or synching manually, it will only synch from 1 to 4 or 5 songs at a time, and then stops, saying the synching operation is complete. Sometimes it will stop synching before the first song is complete. It does this over and over again with varying results. The only consistency is it never completes synching the entire playlist. I've gone through the reset procedure many times, but it still does this. I've double-checked all the other settings and everything should be set to go.
For reference, I have a 2GHz Intel Core Duo iMac with 2GB RAM and I'm running Snow Leopard and iTunes 10.2.1.

Yes to the "restore" question. I mistakenly referred to "resetting" instead. So I've already tried that, many times.
I'll take a look at a different port or cable, and if needed, I'll reinstall iTunes, but I don't expect it will make a difference - this exact setup used to work.
One other bit of background - Autofill works fine when I let the computer synch from my general "Music" library, that is, when it's working from its post-restore defaults. The failure happens when I want to put something else on the iPod, and it happens whether I use Autofill, or drag a whole playlist to the iPod, or drag several songs at a time to it.
In fact, there are only two times it works correctly, 100% of the time - when it Autofills from my "Music" library right after restoring, and when I drag a single song at a time to the iPod.

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