Although I am not a fan of .38 Specials, I had one expressly for the purpose of carrying it concealed. B/C I tend to carry in my pocket, I figured if the emergency ever came up, I might be forced to actually shoot it from inside my pocket. Therefore, I chose a S&W snub-nosed .38 with an enclosed hammer so that the hammer would not get caught on the cloth of my clothing. The aim on these suck, but that doesn't matter if you are carrying with the intent of self protection at close range. (I am a fan of the Springfield 1911A for accuracy and pure pleasure of shooting; but they are not suitable for close range work in my opinion.)
I don't know if you have worked with an ankle holster before, but I find that they are very cumbersome. Your pants go over them, so you have to lift up your pant leg to get to it. Not only is this a pain in the ass, but your movements are obvious to interpret. Furthermore, you put your body in a vulnerable position while doing this. And if you wear boots, you are unable to wear your holster.
That's my $0.02 in general. If you are interested on more input on specific handguns, feel free to PM me and I can blather away til you are bored to tears.
Good luck to you.