Also, what about gear? Few people realize, until they have been abducted by the kayaking aliens and transformed aboard the mothership into kayaking zombies, that the gear is what really adds up cost wise. I guess its why most people go used since one has $400+ in gear to purchase as well (paddles are $200, helmets $100+, PFD $100, rubber chicken $5.34).
So, I'm your boyfriend's size and here are the boats I would recommend:
Real Cheap (don't pay more than $350)
"Medieval" made by Dagger
Reasonable (don't pay more than $450)
"Inazone 240" or "Inazone 242" made by Pyranah
"RPM Max" made by Dagger
"X" made by Wave Sport
You've won the lottery (brand new and over $800)
"GTX" by Dagger
"Big EZ" by Wave Sport
Personally, I think the Big EZ is the way to go (I own one and think its the best ever AND its a good starter boat). You can now find them used and if you go that route make sure you look for chunks missing in the hull (not good), particularly in areas that will be submerged. If you buy a Big EZ your boyfriend will look cool and he will be very happy for at least a year and at that time will begin to buy more boats at rapid rate.