I broke down and bought an iPod last weekend: an 8GB iPod Touch. Might be too small, but I just couldn't justify paying for a bigger hard drive and I was tired of waffling around about which iPod to get, when to get it, and on and on. Costco had a $7 off deal and I had a $60 (Costco) rebate burning a hole in my pocket. Decided I had waited long enough to finally have an easy way to listen to the music I've had sitting around on CDs for years now, practically abandoned. (Very sad. :-)
I picked the Touch over the Nano and others because I want to get used to the touch screen experience. Let's call it a potential practical benefit for my work these days, and leave it at that. :-)
Today I finally completed the many steps required to actually use my new gadget. I stopped by Fred Meyer and bought a tape-for-MP3 device, so I can listen to the music in the car. Also got a car charger, just in case I forget to recharge. Then I moved a copy of my iTunes library - that I've been building over time on the desktop computer (with a big jumpstart courtesy of Tynor, who loaded a whole bunch of CDs for me at one point) - over to my laptop, set it to import all the music, then realized that it also imported a bunch of duplicate albums that I had in "My Music" folders (current and past archives). So weeded all of those out (iTunes doesn't appear to have any easy way to "remove duplicates" so I did it all by hand), and then synched my iPod. Voila! I think I'm good to go!
As a bonus, I can now load a bunch of CDs that the desktop CD drive refused to recognize, so I can add those to my library and have them on my iPod too. Sweet!