Let's see now, after he sells "The Diego" he will be down to his trusty Giant Cypress SX and his new Roubaix. That gives him a flat bar road bike and a fast, lightweight road bike.
Given that he has had 3 bikes, DG will soon be practicing some kind of satanic N-1 bike law.
Clearly he will need to be adding to the stable. What should he get?
Some ideas ...
1) A very fancy beach cruiser
2) A recumbent or trike
3) A full suspension mountain bike
4) A kinda combo of 1) & 2) in the form of a RANS crank forward
5) A BMX bike on which he can do tricks to impress women
I think an eye-catching cruiser, like the Electra Rat Fink or their Rockabilly Boogy, is a good choice. He's in the perfect location to cruise the boardwalk areas. It would enable him to make eye contact with the women walking, roller blading, or biking. The low seat would allow him to sit & be cool as he chats it up with babes. And he would be able to use the line, "Come back to my place and I'll show you my Roubaix."