I have an 8GB iPod nano. My iTunes library is about 8.5GB. However, I only have about half my songs (or about 4GB worth) checked. When I connect my iPod, it won't sync and gives me the message that there isn't enough space on my iPod. I have specified "sync only checked songs" in the iPod sync menu. I have even tried restoring my iPod and then syncing. If anyone can tell me how to get around this problem, other than syncing manually (which I know how to do and HATE), I would greatly appreciate it.