Vista/7.5/HP Pavilion/2nd gen 8gb nano combo apparently doesn't work

There's something about this combo that simply refused to play nicely together. I'm trying to make the laptop (said HP Pavilion) my primary computer, since I've gotten rather tired of the Pentium III dinosaur it's replacing, and this would include using it for my iTunes setup. Problem is that EVERY FREAKING TIME I connect the iPod, iTunes complains about needing to restore the iPod. Then it just keeps complaining that it's found an iPod that needs to be restored. AFTER I've restored the iPod!!!
For now, I'm giving up on 7.5 and rolling back to 7.3. I'm hoping that helps. Does anyone have any idea what is going on, whether it's fixable, and whether 7.5 can actually be used with Vista and a 2nd gen nano without screwing the whole thing up beyond recognition? (grumbling and cursing as I restore my poor iPod from the aforementioned dinosaur)

Another update: I stumbled across a weird but effective workaround:
Connect iPod
Acknowledge message about iPod needing to be restored
DO NOT hit Restore button
Reboot computer with iPod attached
Once computer is booted, bring up iTunes
iPod happily synchronizes as normal.
I have no idea why this works, but it does.

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all the posts I could find that were similar had to do with ipods that were jailbroken and on Windows.
I have iTunes 10.1, iPhoto 6.0.6. running on OSX 10.6.5
iPod Touch 2nd Gen 8GB OS 4.2.1
The Problem: Since I got 4.0 and later, I have not been able to sync photos from iphoto. itunes says that it is, the bar moves and says all photos have been synced, all the photos I want synced are checked in itunes and still nothing when I check them on my ipod. iPod says no photos in album. I tried deleting the ipod cache on my mac, nothing. I tried syncing to a single file folder with the same photos, same. I tried exporting all the photos I wanted synced to a separate folder to jpg and smaller resolution, same result, no photos on ipod.
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I have tried rebooting both iMac and iPod, same thing.
and I hate how I can't just email apple and tell them the problem.
Any and all help would be greatly appreciated. I just can't seem to find anyone else with the same problem.
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Vista/7.5/HP Pavilion/2nd gen 8gb nano combo apparently doesn't work

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