[Elspode]

Here's the sum total of what I've learned about mp3 players so far:

1. Cheap mp3 players usually suck in most important ways such as build quality, features and capacity. That said, the most affordable mp3 players are the solid-state/memory card-using varieties, typically with a capacity ranging from 128 megs to 512 megs as a built in base. Nicer ones will allow the use of a memory card, and one gig cards can be had right now for around $60, give or take. A decent basic player of such a variety will cost you between $80 and $120 if you buy well.
2. HD based varieties offer both vastly increased storage (typically from 4 megs up to 60 megs, with price increasing proportionally as storage increases). Typically, features and usability are also proportional to price. I am using a Creative Labs Zen Touch 40 gig. It performs well, has a nice big mono LCD screen and an interesting, if not always precise, touch-control surface. Disadvantage? This particular model has no bookmarking feature, making audiobooks basically inconvenient, if not outright impossible to deal with. User software to load it up is great, and USB 2 is blazingly fast for the transfer of files. Full album of mp3's at 128k sample rate takes about 25 seconds to load. Ripping takes longer, but that's a different subject.
3. IPODS are awesome, but comparable Creative units can be had for about 25% less money, along with other brands. Creative seems to have the best competition out there among major players, but there are literally dozens of other manufacturers doing a fine job. Archos comes to mind, but their stuff is also pricey. Excellent quality used units can be found on Ebay (that's where I got mine, and it was virtually unused. I purchased it for $70 under best retail price I could find, shipping included).

Bottom line? Research online. Set a budget for the purchase, then go hunting on the Web. Virtually all units will come with their own software for handling the files. Some of that software will rip CD's, some will not, but there are lots of excellent standalone apps out there, the best ones are actually free through Sourceforge public license software sources. Some units will function as a direct "extra drive" with Win XP, some won't, so if stupidly simple ease of use is important, make sure you check that aspect in advance. My new one does not appear as an extra Windows drive, but my old ones did. No big deal in my case, but it might be in yours.

Good luck!