I use a Topeak Turbo Morph G pump. I like it better than the gauge on the road morph gauges.
Kevlar helps in tires, but it was made to stop blunt bullets, and doesn't do quite as well with sharp cutting punctures.
CO2 usually fills the tires up "mostly", and they should be finished off with a pump. If you have trouble pumping, carry CO2 and a tire pressure gauge. You can try using 1+ cartridges. Get a CO2 unit that screws onto the valve.