When I got my iPod (I'm on #2 now) I figured I'd get all sorts of music from iTunes. However, after I converted my CD collection with RipDigital's service, I haven't purchased more than a few songs a month.
Instead, I find myself turning to Audible.com for my audio-fix. I use the Podcast feature from iTunes to listen to a few podcasts, but I'm doing most of my listening on Audible. I was actually an Audible listener a few years back on my old Rio 500, but the iTunes integration really sold me. You download the Audible files using a small browser-helper application and they jump directly into iTunes from there.
Most recently I've been listening to the Ricky Gervais show, which is apparently the most successful podcast ever with about 250,000 downloads per show. Audible makes your subscriptions available via RSS (with Enclosures) so I just subscribe to those in iTunes and they just show up. The whole season is only $7 - I listen to this on the small flight to Seattle.
UPDATE: Doh! Al reminds me in the comments that the best part of signing up is the $100 OFF a new iPod.
I'm in the $14.95 a month "Gold" plan that gets me a free New York Times (or WSJ) subscription via podcast with one free book a month (and rollover). I used to get 2 free books a month, but I can't listen THAT fast. This plan is WAY better than the $9.95 plan, which only gives you 30% off. I'm all about free.
My favorite audiobooks:
Their list of compatible devices is pretty impressive. The current promo is two free books for a 30 day trial.
Scott Hanselman is a former professor, former Chief Architect in finance, now speaker, consultant, father, diabetic, and Microsoft employee. I am a failed stand-up comic, a cornrower, and a book author.
Disclaimer: The opinions expressed herein are my own personal opinions and do not represent my employer's view in any way.