My iPod no longer displays artwork for certain albums

Ok, so here's my problem. Every so often when I alter the artwork on my iPod with iTunes, I have to reset the artwork by clicking the "display album artwork on your iPod" checkbox in my menu, then clicking apply, and repeating the process to redisplay them. If I don't do this, sometimes I wind up with a black box where the artwork would normally be displayed when I peruse my iPod. I know that this is a common problem for some people so hopefully there are some on this site and know what I'm talking about. Anyway, to my current problem, when I attempted to do that last night, it was just about at the end of the progress bar when an error message appeared that said "The iPod 'name' cannot be synched. An unknown error occurred (-50)." So, because it didn't complete the cycle, certain albums no longer display the artwork. It's still there on my iPod when I go into iTunes, but when I go through the actual menus on my iPod such as Cover Flow etc. I instead see that annoying box with the musical note in it. Has anyone come across this problem before? I would very much appreciate a solution

I just tried it again and this time a different message showed up "The iPod 'name' cannot be synced. The required folder cannot be found." I have no clue what folder it could be talking about.

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