2nd Gen 20 GB - December 2002 until August 2003. I was still on Windows at the time, and was one of the rare few that used MusicMatch Jukebox to sync my iPod before Windows iTunes came out. The headphone jack was shorting out and I brought it back to Best Buy where it was purchased and traded it in for a new...
3rd Gen 30 GB - August 2003 to Today. Still going strong with good battery life, though I mostly use it connected to a charger in my car or connected to a charger on my home stereo. The best iPod design ever in my opinion. I've put off upgrading to a larger capacity simply becasue I love this style.
1st Gen Mini - March 2004 to Today. A pink, for my girl's birthday. Man was this hard to find, the pink ones were popular. Lucked out at CompUSA because they happened to get a shipment with one pink one at the time I was in the store inquiring. Still works great because it never really gets used at all.
512 Shuffle - April 2005 to Today. Works great - Only gets used for exercise.
The Future? Unless my 30GB breaks, I do not plan to buy a new iPod until capacity hits at least 80GB (preferably 100GB).