I have done exactly this thought experiment on a couple of occasions.
An S&W 317 .22 LR
A brace of stainless Airweight J-Frames, either Bodyguards or Centennials of one model or another. I think I'd prefer .357's, although they would get carried with .38's. These would be pocket and AIWB guns.
A pair of Model 66's, with 4" barrels. These would be the main concealed carry guns, with .38 Special +p's or the more moderate .357 loads.
A stainless GP-100 4". This would be the "woods gun" and would be loaded with some sort of heavy, rompin' stompin' robot killer loads.
Once I'd gone that far, I'd have to have some sort of .357 lever gun too. Preferably stainless as well.