Check out Firmstrong cruisers. They have simple, easy going bikes that'll fit the both of you at a price within your budget. He needs to look at the "Chief" because at 6'3" he's gonna need something XL. Later, should you decide to get more into cycling (or decide it isn't for you) you can sell cruisers easy on Craigslist.

FWIW, my wife loves her Specialized Roll and I highly recommend it but you'd need to more than double your budget to buy two.

Good luck!


-Kedosto