PurposeAre you planning to use your new player while exercising? If so, you might be better off with a flash based player like the Shuffle and Nano. Running and shaking can cause the hard drive based players to skip, crash, and otherwise stop playing music. Do not let that "3 minute anti-skip" crap fool youâ€”they don't work well when used while exercising. This is the primary reason that Sarah got a shuffle and she loves it.
SpaceDo you really need that space? Possibly not. First, do you even have 5,000 songs (that's how much you'd need to fill up a 20 GB player) on your computer? If not, why get the 60 GB beast? Spend the extra $100 on music!
Another thing to consider for this point is how often you will be updating your player. If you are fanatical about your playlists or just by habit happen to dock your player several times a week (remember: the more you listen, the more you've got to charge!), you can probably get away with a very small player since you won't need to carry your entire collection with you all the time. To accomplish this, setup your player to populate with new stuff every time you plug-in (automatically).