Doc,
I too carry my 442 99% of the time in my left front pocket. People tend to fixate on the strong side holstered weapon that is visible, and do not suspect that I have a full firing grip on my J Frame. It appears very casual, yet is as ready as you can reasonably be. I also dedicate a fair bit of my J frame practice time to left handed operation of the BUG.
As far as a basic 5:
For me, it covers recreational plinking, concealed carry/self defense/home defense, hunting and competition. Very basic actually.
I am not a stickler on some. The Ruger MKII could be replaced with a Colt Woodsman, Browning Buckmark, or some other high quality .22. The 1911 could be a Colt Lightweight Commander, etc. Though if a person is only going to have one 1911, a 5" Govt. Model is right at the top of the list.
The 5" Model 29 covers hunting, hiking, and all other manner of outdoors activities. In fact, I can think of no finer outdoorsman's sidearm than a 5" Model 29. Not a bad home defense gun in a pinch too.