It is clear that you have put some thought into pocket carry and have reasons for doing so.
I started out pocket carrying, but only because it was convenient for concealment.
It didn't work for my defensive training classes, so I went to IWB in a holster.
I have found OWB much more comfortable. Either a shirt tail or a sport jacket serves for concealment.
I have quit carrying a light alloy revolver, and a steel revolver for backup is a little heavy for pocket carry. I can see carrying an LCP II in a pocket holster, but it would have to be in a vest or jacket to allow drawing while sitting.
.380? Not optimal, but I wouldn't turn it down.
I won't recommend how to carry to anyone else, but I will urge that they consider all aspects.
I'll share this story: a friend who is a former long-time senior police officer chose not to carry after leaving the force But he reconsidered.
He bought an LCP competitor in a closable purpose-built back pocket carrying set-up. After a while, he changed to IWB with a large double column pistol. Neither of those works for me.