I have arthritis in my hands, elbows, and shoulders. I don't shoot 44 mag any more than is absolutely required for hunting nor do I shoot 357 mag in lightweight handguns. I don't find any 22 difficult or painful but lots of rounds will cause pain from the continued gripping stress.
I shoot Ruger 22 pistols both right and left handed w/o problems. My biggest difficulty stems from loss of strength and I've found I can no longer easily handle the DA trigger pull on my 9mm carry pistol while shooting weak hand.
Just my opinion but your friend's problems may stem from simple unfamiliarity with handguns.
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