jared,
Are you wanting to multitrack straight to one of these software programs, or are you mixing from something else (standalone DAW)? I have used Cool Edit Pro a bit, and find it to be easy as hell to navigate, and think it sounds very good. Historically, I have tracked to a stand alone unit (Yamaha AW4416) and then mix to CE Pro. Very easy and I can highly recommend it. They have excellent tech support as well. Good luck.

Rob

jared,

if you will be doing MIDI, cakewalk is definitely the best. for straight audio, I'd go CEP 2.0

I am recording directly into my computer through a Lexicon Core2 (grumble grumble). I don't use midi, just regular audio, and at most 4 tracks at once.