The whole soundtrack is great, but the 600AD overworld theme and the Zeal theme are two I could listen to over and over again.

Funny you say that: Amazon's price for a classic just jumped $50 since Tuesday.

MediaMonkey has good iPod support, and has for a while. It is also *far* superior to iTunes in its ability to manage large music libraries. once you get over about 10k tracks, iTunes slows to a crawl. I dumped iTunes about 4 years ago, and I've never looked back.