As you mentioned, the j-frame is easy to carry most anywhere. The laser grips are useful in an offensive roll, but I'm not sure about defense. Anyway, they're nice just the same. As for 'only' five rounds, that's usually enough in many recorded shootings although more is always better.
In any event, it appears that you like the Kimber the best so this may be the solution. As I type I'm wearing my j-frame as it is in fact, the easiest carry I've ever owned in 30+ years. BTW: I voted .380 assuming you intended to type .38 snub.