If you wanna listen to some good rockin music try Britny Fox!

I also love the turntable. My iPod is a priceless tool while away from home. I wish itunes and amazon would have bitrate options!

This is old, but...
I would suggest ditching iTunes completely and getting your iPod hooked up with RockBox (http://www.rockbox.org/) if it's supported on your iPod's generation. RockBox can play almost every file format, including FLAC. FLAC is my favorite file format, it's huge (300MB per album and up) but completely lossless.
As far as quality goes, you're not going to get a lot from iTunes and Amazon.com. I don't know what kind of music you're purchasing, but I know emusic.com sells everything at 256kbps VBR mp3. Either that, or purchase your music in physical copies and rip them onto your hard drive using something like Exact Audio Copy, that way you'll have full control over the quality you'll get.

I've heard a bit about RockBox lately and it sounds really cool. How hard is it to get your iPod hooked up to it?

I'm not entirely sure, because I own a Creative Zen, and those aren't supported by RockBox yet, though it's being worked on. I assume it's not very hard, you should read the website, go through the steps and see if it seems like things you'd know how to do. I know a decent amount about working with computers, but your skill level might be different.

Awesome, thanks, I'll be sure to check it out!

PS new here (should probably introduce myself!)...I live in DC, work in marketing, and went to college in NYC. My office is really laid back and actually encourages us to keep music on our computers and share it through iTunes. It's been a great way to find new bands! Hoping to pick up more here!