If you look, you can get a toshiba 2200 for $210 shipped from mercata. That is what I decided on. It pretty much has all the cool features you need, and is pretty high quality, IMHO.
EDIT:
Thena again, with your friend's set up, he would be just as well off with a 4 head VCR, honestly. With no surround or nice TV, teh benefits of DVD cannot really be seen. Unless he plans to upgrade in the future, that is.