There are also games that depend on a variety of skills, SET and Blokus come to mind. Settlers of Catan and Apples to Apples develop social skills, but need 3 players.
In a way, being around older kids might solve some of his 'no one to play with' problems. Hint, Hint.
As for chess - I reccomend that you study up a bit and come back and become a challenge for him. If you enjoy that sort of thing, I know I do. I've been playing DS Chessmaster, the art of learning all summer while my son was away at camp. Lots of basic chess stratagy books at your library too.
I agree that Chess Clubs are a natural, too.
Smiles,
Grinity
