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You should be fine with the HP assuming you have normal arms. It's mainly the time to pump rather than difficulty.
One thing someone else suggested in this thread when I was looking for a mini pump was to get the medium version. I ignored it because size was no.1 priority (I was actually looking for something smaller than the Lezyne). However, if it's going to live in a bag or strapped to your frame 90% of the time I would also say get the medium as its still very small and the weight difference is negligible.
Specs
SMALL: 170mm | 77g
MEDIUM: 216mm | 90g
hugo7
The Lezyne "High Volume" pumps state 90psi max; is it going to kill me to get it near that with a hand pump?
I have 4 bikes with 35c tyres at 80psi but 1 MTB with 2.4" at ~40psi.. not sure if I should go for HV or HP.