I have my old Nomad and been thinking about buying an iPod. For now my main use comes out of a I-O data mp3 player. I love the fact that it's so tiny. I just clip it to my bag and I'm good to go.
It's controls are simple, sometimes a little too simple but considering its size, its understandable. The sound quality is great. The compatibility is never a problem and it work on both my macs and PC's with all types of OS's. The software is simple yet detailed enough and they give you everything you need from the USB cable to the battery to a detachable belt/strap clip. It comes with an onboard 64mb and takes 64mb MultiMedia Cards for easy expansion. I bought mine for $40 at outpost then bought a $30 MMC from TigerDirect so it holds 128mb. It also doubles as a convenient mini USB HD where I take files from work home, and back. It may not be the best featured but I think the price, memory, and size make it the best in its class.
p.s. I bought mine at outpost for $40 but they sold out.
http://www.tigerdirect.com/applications/SearchTools/item-details.asp?sku=I226-5000 P
I have tried some others but I really enjoyed the little I-O data model. I-O makes a newer model but it doesn't seem to have any expansion? You can get CD players too that read CD-R with MP3's. Those are decent but If I wanted that big of a size, I would have bought a jukebox HD MP3 player instead like an Ipod. I don't listen to CD's anymore anyways. I buy them, convert them all to MP3 and keep it all digital. Even if I play them off my stereo, the reciever is fed by a line ut on my sound card. If you want the functionality of a CD-R reader, I can't really suggest a particular model since I don't use them. My friend just bought this one and likes it. It has a fairly long EASS (anti shock) and the size and controls are nice. Price is great too. Even came with a car kit so its all around a decent p[ackage IMO.
http://shop3.outpost.com/product/3430883/
As for HD's I really don't like anything but the iPOD's Besides, yo won't get anything decent for under $100
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Hope this helps a little. Its just some of my preferences. Doesn't mean you should run now and buy one.