i've had an iPod video for about 2 years now. It still works, but the screen has a fairly thick strip of dead pixels that take up about 10% of the screen area. The one huge problem I have with my iPod (which has been going on for about 8-12 months now) is that it does not turn off. Ever.
Ever since I purchased one of those cheap iPod docks with speakers, my iPod has refused to turn off ever after resetting it, deleting everything off it, plugging it in, removing it from power, etc. No method of trying to turn it off works. Fortunately its battery life is still about 12 hours of just laying in my backpack and about 3-4 hours of actual music listening.
Also, I don't know if it is the fault of my iTunes software or of me not knowing how to set things up, but I could never get my iTunes to automatically add files to the library/sync them to the iPod unless I manually chose "add files from folder" from the menu. This is despite the fact that "add files manually" was never selected in the options.
Basically, iTunes is a nightmare to me and I'm absolutely sick of it and would like an MP3 player with at least 10GB (preferably at least 30GB) that comes with non-buggy software that allows music that I download to a specified folder on my computer (say, C:\Music) to automatically sync to the MP3 player when I plug it in.
Oh, and support for audio scrobbling would be nice too (last.fm)