I'm a tool snob and would rather have few excellent tools than a lot of crappy ones. Which is mostly because we have the latter and I'm sick to the death of them. We do have most everything we need, though... but still I'm quietly assembling my own toolbox of excellent tools 
I'd say a work stand is an excellent gift. Tools you can buy one at a time, but a work stand is more expensive and more of an investment. It's incredibly handy once you start working on your bike. I have one of the Park Tool ones, it's good.
It depends what he wants to do/already can do, but I'd suggest that after a work stand he needs the basics to fix a flat, but he probably has that, then the basics to clean+lube his bike, probably has that too, then the stuff to adjust gears and brakes- allen wrenches, a couple of small screwdrivers, needlenose pliers are handy, a good book on repairs? Then come the tools you need to change your drivetrain and remove bottom brackets and suchlike.
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett