Before I invested in the iPod, I purchased a new set of earbuds off eBay for little more than a song to use on my development machine at work... my other headphones had finally bit the dust, and I wanted to see if I could tolerate the earbuds before handing over cash for the iPod.
Finally took the plunge several weeks ago and purchased an iPod. I managed to get a good price from Apple's Refurbished site on the iPod Photo (one version removed from the Video) - 20GB for about $100 - hard to beat, and shipping was super-quick.
Anyway, I really like the sound out of the device, MUCH better than I anticipated, and I generally like the user interface. The games that come loaded on it are simple but fun, and the contact management/calendar were nice features that I didn't expect.
I'm not partial to iTunes, and would rather find another way to load music to the thing but it's pretty much the only option that I know about.
If you have a larger MP3 collection like myself (mine's about 45GB) it'd probably be easier to get an iPod with a bigger drive. I would be happier with the 60GB model just because I wouldn't have to pick and choose through my collection - I could just do one mass load and not worry about it for a long time.
Overall it's a nice little device, and helps me tune out the world while I'm coding away in my cube. I'm not burning up CPU cycles with Media Player or MusicMatch while listening, and the sound quality is tons better than just playing through the headphone jack of my PC.