EJ, you do truly live in Paradise- more so than me, even! I am envious. As for the bike tires, yeah, you might try the pressure thing, but then he'd have to pump them back up every time. (That might get old quick.) A second bike is the easy
answer, with a second set of wheels also right up there.
The flip side of the coin is to get a different bike rack for the bus if this is any sort of common problem/complaint.