I've have a $30 iriver for years I got on ebay. It's really easy to use. I just got an ipod nano and I think I'm taking it back 2morrow. I don't like messing with that itunes bs either. I'll spend $40-50 on a new iriver and pocket the $100 I get from returning the nano. Or I might get a shuffle. I don't know. I'd still have to mess with freakin' itunes.
easy controls, easy software, cheap- Iriver from ebay
looking on reviews on Cnet it looks like to Ipod Shuffle is perfect for gym and can take a couple of licks and keep going