So I decied that my first first pistol will be a .22 pistol

[Texfire]

I'll make an arguement for the Buckmark. I have one and love it. Also, though this was a total coincidence, my choice in 9mm was a used Browning BDM. So the grip shapes of the two firearms were very close, which I think aided a smooth transition. I find that the grip angle of the Ruger is rather extreme, so you might find that the Buckmark will allow a smoother transition.