I paid for the 64gb Ipad (1 not 2) a few months back. Glad I did, because I'm always loading it up with audio and video podcasts that I don't get time to watch right away.
Depends. The 64GB iPad holds 16,000 songs, or 80 hours of video. This is not including Apps.
The 32GB holds half of that, so whatever you think you need.