Problems with artwork displaying in iTunes but not on iPod screen

I have iTunes (7.6) and a 5th gen, 80GB, firmware 1.2.3 iPod.
Not infrequently, I find that a song's artwork is visible in iTunes, but not on the iPod itself. Sometimes the artwork is displayed simply as a black rectangle on the iPod.
The converse situation also sometimes happens - when album info is retrieved from the CDDB, sometimes album artwork is also retrieved - but this is not displayed in the iTunes software, only on the iPod.
And yes, the "Display album artwork on your iPod" checkbox is selected in iTunes.
Does anyone have any more info about this?
Are there any restrictions on image file formats? Maximum size? Type? Interlaced or not?
Last time I asked this question I got zero response
It is an irritating problem, cos there's no way to check what the artwork looks like on the iPod without disconnecting it from my PC :/

OK to drag this thread back on topic:
I think the "sync" thing is irrelevant anyways.
What I tried in the end was viewing my iPod in iTunes,
navigating through to the check box for "display album artwork",
UNcheck it, and click apply.
At this point, iTunes said, with NO confirmation "Are you sure?" dialog, "DELETING ARTWORK ON iPOD" !! :-O I was not pleased
However I then re-selected the "display album artwork" box and clicked Apply. The process took about 10 minutes to complete.
When I then disconnected the iPod, the black squares were gone, and the artwork was NOT deleted (phew!) and was displaying correctly. I was pleased
The amount of "other" megabytes on the display in iTunes for my iPod's contents had shrunk.
I dunno what all this actually did - are the artwork files embedded in the MP4 files on the iPod? Or are they stored seperately and linked to them?
I'm wondering if the "black square" thing is caused by an MP4 having an embedded image, and there also being a conflicting image file elsewhere on the hard drive? But this is just guessing.

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