There are a lot of great albums (obviously, I would hope). Hot Rats is deservedly regarded as one of his best in his jazz-fusion idiom (other good albums in this style are Waka/Jawaka and The Grand Wazoo). In the Mothers period, Absolutely Free (which is a strong influence on a lot of progressive rock) is really amazing, as is We're Only in It for the Money which is a fantastic Beatles parody. Uncle Meat is a nice overview of his more experimental tendencies. Freak Out! is also regarded as one of his strongest albums but I suspect it isn't the best place to start; it wasn't until I got into some of his later albums that I really saw the appeal of it. Apostrophe (') and Over-Nite Sensation have some of his best known songs and are probably among his most accessible works. My personal favourite may still be Läther, which is also the album that got me into him. It's three hours long, but it covers nearly all of the styles he played and does a good job demonstrating the appeal of each of them. This isn't even close to a complete list but I'm probably pushing the length of visitor messages here so maybe I'll post more in another message.
I've honestly been half-considering it. Or just teaching English or who knows. It can't possibly be more miserable than retail. I really want to move to D.C. but who knows if I'll be able to find something there. I'm working on my résumé first and will probably shop it around and whatnot.
Hope your students do well.
