I have a couple of the handguns that you have referred to, and have shot many of the others. For me, there is a real difference in what each one can do well. I'm lucky enough to have several that I can choose from in different situations.
I carry crossdraw IWB, or in the pocket. My thoughts on what I carry and some that I don't...
In more "dangerous" situations, I can carry my SIG P245, XDm 45 compact, or XD mod 2 9mm IWB. These, of course, are much too large for pocket carry.
My Kahr CM9 is probably the most carried handgun I own. Very small, lightweight, highly concealable, inexpensive, shoots great, and has been 100% reliable. In larger size pockets, you can pull off pocket carry with a decent belt and holster, but is just slightly big for that.
I usually carry my SIG P238 IWB Crossdraw in situations where concealability is the greatest concern. It just disappears along the waistline. I like it enough that it is the only handgun that I own that has a manual safety. The Ooohs and Aaaahs just flow everytime anyone shoots this gun. A phenomenally sweet shooter. It is better as a pocket pistol than my Kahr CM9, but it actually weighs just about the same, so can be a just slightly heavy for that role.
The truest "pocket" pistol that I own is the Taurus TCP. I call this my "dirt" gun. This is the one that gets dropped in a pocket (with a pocket holster, of course) on a quick trip to the store, while wearing gym shorts, doing the dirty work out on the property, or believe it or not, even wearing PJ's around the house. It is extremely light, thin, and you can totally forget it is even there.
The TCP is the handgun that keeps me armed almost all of the time. It has been utterly reliable in my male friends hands, but I've seen several FTE in some female's hands...so I think it is sensitive to being limp-wristed. I bought it for one reason and one reason only over the Kahr CW380 and Ruger LCP; I had a coupon at Cabela's and was able to purchase it for about a hundred bucks.
I've never understood the little Glock 380; it is a 380 the size of my Kahr 9mm.
Happy handgun hunting!