If I did not know what he really likes, and going by your price range, I would guess he might like the following (they do not have a wait list where I'm from): Defy El Primero 21 in carbon case and titanium bracelet, IWC Big Pilot, GS PanoInverse, PAM01036, or JLC Polaris Chronograph WT/Chrono.
I would of course suggest the speedmaster professional as the best however.