I've got a friend (no, really) with an iTunes problem. It's on a Windows 7 PC and he has a 256GB iPod, more than sufficient for his 150GB music collection.
The problem is that chunks of his music don't make it across at sync time from iTunes. After investigating, it seems that the missing music is all on compilation albums and that the iTunes 'Artist' and 'Album artist' fields are possibly to blame. We've filled these fields in within iTunes for the missing albums but they just don't make it across to the iPod.
I've already tried consolidating the library and restarting the PC and doing multiple syncs.
Very strange. I wondered if anyone can think of something else to try?