Odd iTunes 5 issue

Hi everybody.
I'm having an odd issue, though I'm not sure if it's my iTunes 5, or all of my OS needs fixing. I'm having three main problems:
1. Neither one of my iPods will show up in iPod updater, though they show up normally on the desktop.
2. They show up as "generic" iPod icons in the iTunes source window, not the proper icons.
3. The option for "show album art on iPod" isn't under iTunes pref when a iPod Photo or my Nano is plugged in.
I plugged them both into a friend's iBook to update them, and had zero problems.
I trashed com.apple.iPod.plist, and iTunes.plist, to no avail. I actually deleted and reinstalled iTunes as well.
I have no idea what's wrong here, but its quite frustrating.
I'm on a Dual G5 Powermac running 10.4.2. Both iPods are fully updated.
Any ideas on what I could maybe do?

Well, problem solved. After much frustration involving restarts of both machines and a reinstall or two of iTunes on the PC, I did a bit of hunting around on some tech forums, as well as some testing on my home network. Turns out the NIC drivers on my Windows desktop were to blame. Uninstalling and reinstalling the drivers from the motherboard's manufacturer disc did the trick.

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Hi,
I'm sure this is really simple and over time i have completed complicated the issue and i just need some clarity.... here goes....
SET UP
Synology Nas with a share on it called iTunes (for the purpose of this lets call it the U:\)
Desktop pc running windows 7 ultimate
mac book pro retina with osx
Apple TV
iPad mini
iPad 2
iPhone 5s
iPod nano (6th Gen)
History:
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My Current settings:
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My Current File Structure (on the iTunes share)
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U:\iTunes Media Folder\manual copy\iTunes library folder - DO NOT DELETE OR MOVE!! - 32.5GB, 4503 files
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if you need any further info / screenshots please ask.
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Thanks for the reply, i double checked and everything on both pc and mac is set right:
both are opening the same .itl file
both have the media folder set to <NAS>/iTunes/iTunes Media
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So this is exactly what happens step by step, after having just restored from a backup:
PC
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Exit iTunes
Wait a minute or two whilst anything saves etc (just incase)
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open Itunes on the mac (its already pointing to the right library)
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wait a minute
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open iTunes on the pc again
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exit iTunes
wait a minute
Mac Again
open iTunes on the mac again
"updating iTunes library" - really quick again
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exit iTunes
restore from backup again
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Any ideas?
Regards,
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