What you have on your Ruger is a trigger shoe. You might try taking it off the trigger and seeing if you like it better without it. I never did like them because my finger would only pull on the edge of it, causing me to pull the shot to the right. I guess I have stubby fingers.

On your .22' s, my guess is weak magazine springs. Also, you may have to polish the ramp that goes up to the barrel. I assume that you' re not trying to feed .22 LR into a .22 short pistol. Any .22 LR ammo should work okay in a pistol made for that round, unless there is a problem with the pistol like I mentioned above. I' m sure there could be other causes also. Have you tried round nose bullets?