I Need a New Musical Toy (phone, cost, transfer, headphones)

[kinkytoes]

Hi All,

My CD walkman finally died, so I'm looking for a new portable music device. Is the i-pod passe? I would like:
1. A machine I can use w/ high-impact cardio workouts.
2. Something that can interface w/ my computer.
3. A device that gives me the option of using standard headphones.
4. A device to which I can transfer songs from my CD easily.
5. A device that plays videos (to feed my youtube addiction).

Ideally this thing would cost under $300 bucks. Way under... Advice?