Since you live in the PRK (people's republik of kalifornia) I suggest a .45. My first gun was a .45 and it wasn't a problem to shoot, recoil wise. It is certainly better than a small frame revolver in .38 (which should be equivalent to a 9mm). Also, since he will be limited, by law, in capacity, it doesn't make any sense to me to carry a 9mm with a magazine limited to half capacity, esp. since the grip will be large with no real benefit.
A single stack .45 will hold nearly all the rounds you would be allowed anyway. The problem will be staying within his price range. Personally, I would never buy a gun solely by price. A Ruger, however, would be my choice in this case. Any new 1911 worth shooting (and one that is reliable) will run more tham ~$350. The only other thing I can think of is to buy a milsurp 1911. If he wants to go to the $400-600 range, I would think (in order of price) CZ 97, Springfield, Kimber, and the Beretta Cougar.