For a floor pump, I have Topeak Joeblow sport pump (about $30 on nashbar). It's easier to put on the valve stem than other pumps I've borrowed when I forget to air up, and supports presta and schrader tube types. Be careful not to force the pump off the stem, as you can pull the damn thing right off your tube. I did that once when I was in a hurry. Then I got to replace my tube When I put it on, I keep my thumb over the hole for the schrader tubes (it's on the opposite side as the one I'm putting on my bike) to keep air from coming out.

As for adding air, I do it every couple of days. I inflate to about 110 psi.