I think you need to try different carries, as suggested previously. I'd try 3 oclock. If nothing works then I'd try the pocket pistols. I carry a Kel Tec P32 in my front right pocket in a cheapie De Santis pocket holster, and it works great. Draws easily, holster keeps it upright, doesn't print. I sometimes switch it out for a 238. It's a little bigger, and does print a little more in some pants, but does carry well. I use the same holster. I've tried the wallet types, and they just don't work for me. Good luck to you. It doesn't matter what you're carrying if it isn't comfortable.
Hmm. That could be part of the issue. Try it from 12 to 3 since it's a straight drop. If it's adjustable, give it 7 to 15 degrees or so of cant and try it again at 4 o'clock.
I think pocket carry is the way to go for someone who wants to carry concealed all year long. I also have a minimum caliber that I will carry and it's .38 SPL or 9mm. I have pocket carried and like the S&W 642 and the Kahr CM9. I don't like to change from one gun to another nor change the style of carry.
a 22 mag is actually a nice round. I'm not a small caliber kind of guy, but the ballistics on this round are nice. However, I would still feel underpowered
I use a Smith & Wesson 638 in a pocket holster. Had a trigger job done on it and she shoots like a beauty. Plus in jeans or khakis it really does a nice disappearing act. Smith and Wesson Bodyguard for deep concealment in basketball shorts or similar clothing.