My SO John is a darn good bike mechanic and he takes care of my bikes, even airing up the tires before each ride. He has a cranky old Zefal floor pump that he likes but I don't get along with it. So I went out and got a $20 Serfas floor pump at REI. It has two holes on the head, one for presta, one for schrader, and a gauge too. It works great and now I can air up my own tires easily.

I air up at every ride, or every other day or so. I carry a small Zefal pump on my road bike, plus CO2. I also have a Topeak Roadmorph for touring and commuting.