I have a 40 Gig iPod G3 and a 4 Gig iPod mini, same vintage. I have a 1 Gig SanDisk Sansa too, but that doesn't count
I buy accessories anywhere. Previous vendors include Amazon, Best Buy, Target, and Woot! .
For accessories, I have an Altec Lansing InMotion, Sony sound isolating earbuds, Sennheiser earbuds, Philips "virtual" surround earbuds, Griffin iTrip FM radio interface, and an iPod sock., among other things.
I use a low-tech adaptor cable to listen to (my captured lossless) iPod content on my audio system. Home theater it ain't.
I listen to Alpha Sierra Charlie (Don't let 'em get you down, Adam!
), The Onion, The (BBC) Today Show, Garrison Keillor's Writer's Almanac, TWiT, DiggNation, and Coverville. I would listen to more if I had more time.