don't bother with iPod - the battery life on their things is terrible - plus the iTunes app becomes a major biatch after a few months of using it to synchronize your playlist.
you can't possibly go wrong with an iRiver H120. The Creative Jukebox Zen Xtra or the newer model, the Zen Touch is also a primo player.
I wouldn't even
consider anything else on the market in terms of quality players at good price points
Prices and features (canadian dollars)
prices pulled from Compusmart - it's a canadian company and they should have a store in your city if you dont want to order off their website.
-20gb iRiver h120 @ $469 - has every feature you could ever ask for. voice recording, fm tuner, and doesn't require software. I have the 40 gig model. It's also the sexiest mp3 player on the market. You could also wait a few weeks for the H3xx series to come out - those are built entirely out of carbon fiber and have color screens (comparable price too)

-20gb Zen Touch @ $399 - costs a bit but you can't go wrong with the 24 hr battery life). Plus you get the amazing audio quality offered by all Creative Labs products
-30gb zen xtra @ $449 - spectacular sound quality but a bit bulky.
-20gb ipod @ 429 - no features built in whatsoever aside from a few cheesy games. Apple claims 12 hour battery life but it's nowhere close to that. You're only paying for the Apple design here
-4gb ipod mini @ 349 - same lack of features as the regular ipod but in a smaller format. Not so great battery life
-4gb Creative Nomad Muvo2 @ $253 - Same spectacular sound quality of the Zen Xtra, 14 hour battery life, same size as iPod Mini
One final option:
-20gb Dell Digital Jukebox @ $399 - don't laugh. This sucker is built by Creative labs and offers the same features as the Zen series of players but in a design similar to the Zen Touch.