The Dell is made by Creative, it has the same internals. If sound quality is important (as it is to me) then only load Lossless WMA's. They are a bit larger, but get real. I have 42 albums on my 20Gb Creatve Zen Touch and it's only 25% full so far. And then look into decent headphones. The Sony's mentioned above are known for their bass, in fact most reviewers think they have too much bass...boomy even. Some love them though. In the same price range but more accurate all over are the Sharp MD-33 and Panasonic HDJ50's (I got those from Buy.com for $20 shipped, love them!) Note, headphones have a break-in period, a good 50 hours is the norm. Head over to the Head-Fi forums and do some learning. Also, those above are all Canalphones, they fit in the ear, super comfy...and super blocking of outside noise. Not suitible for some uses though.
Just use WMP10 to do all your ripping, converting to WMA lossless. You'll need the wmp 9.1 lossless codec.....free.