I looked into one of the local Bitcoin machines near me, but there's still a lot of KYC stuff you have to do at the machine I was looking at. Seems like you should just be able to put in money and have it spit out a piece of paper with an address that has Bitcoins loaded into it. Have you heard differently?

You should talk to @thedamus about it. Maybe he could help you figure out what it would take to get started.