Look at Specialized's floor pumps. I've found them to the most reliably easy pumps to use.

I've definitely had some PITA pumps, including a Blackburn that never seemed latch on to my valve properly and a Joe Blow with a head that fell apart just outside the 60 day warranty period.

Specialized's Airtool comes in Sport, Comp and Pro models ($ to $$$). I'd go for the Comp as it has a metal base.

Also, get a CO2 pump to carry with you on rides. And buy extra CO2 cartridges so you can practice.