Um, for the record, you can load mp3 files into an ipod. You don't HAVE to buy your music from the iTunes store. If you buy it elsewhere online, just make sure you buy mp3 format, and if you buy a CD, you can just rip it. I think it just doesn't do WMA files, but I never use those anyway.
I have never had a problem with iTunes syncing with my 30GB iPod video. I've also been using iTunes since it came out originally, and I have never had a problem with it.