I've got an iPod colour. I got it cheap off eBay (brand new too) about 2 1/2 years ago. Otherwise I was looking at the Zen touch at the time. The headphones it came with are totally shit but the rest of it works very well indeed.

Although it doesn't have that many functions as the cost of a simple design, it is really easy to use. iTunes doesn't reall bother me, it's essentially just drag and drop but with an iTunes window instead of explorer. Getting songs off the iPod isn't so easy as it stores them in a number of oddly named folders, but this isn't too much of an issue as the music would've been on my computer already.

I have it with me every work day, although I don't always listen to it. Sometimes on the train, bus and tube you need to just have some tunes. Also helps gee me along a bit if I'm walking to the station.