And that car thing...
IMO there are three things that impact the level of comfort carrying and shooting these things: 1)Weight 2)Ammo 3)Grips
Weight is just that simple, but this is also a big factor with portability, especially in regard to actual pocket carry. All of these things get bigger and heavier when you shove them in a pocket and start walking. Three ounces is a lot, IMO, when it is banging around in a pocket of dragging down an elastic waistband.
Ammo is a huge variable, and the reasonable choices would be 38, 9mm and 22LR. There are lots of 38 options, and with reloading (you do live in a house now...) even more so. 9mm gives you ammo compatibility, but no Smith option, and the LCR is molded over the stainless frame (as is the 357, the others are molded over aluminum) and they are heavier and more expensive than the 22 and 38 versions. As has been mentioned, 22LR might be the overlooked option. Ammo is on the shelf again, you could get a 43C or LCR, or if you didn't really plan to put it in a pocket a 3" 317. Claude is the big j-frame EDC advocate and he is using a 43C. With any of these options you could shoot thousands and thousands and thousands of rounds, all while having the dog walking gun. Maybe later there is a 38 or 9mm or 357 mate. And if your wife has any interest in this at all I say the 22 has a big advantage.
But grips are the part of this that I think has been under discussed. If it is not actually in a pocket or the pockets are larger there are a lot of advantages to something larger than the little boot grips. There are a bunch of options but I like the Altamont Bateleur on the J, and the Hogue that Ruger ships on the 3" guns sure look interesting.