I've always used the FLV Converter found at http://www.flv.com/flvconverter.html. It'll let you convert to MP3. I tried it initially because it was free. It works for my needs.
I know less about the west coast, but friends from there swear by USC. What are looking to study while at school? That info might help with recommendations.
Is a Mac a must? It sounds like he would further ahead to get a small netbook or something similar. Also, why look at getting 5 year old machine? I don't think it would last very long.
Well written with good imagery. I could easily see it as a voice over the closing scene of an asian martial arts movie, but maybe that is just my overactive imagination.