Barnes and Noble has exactly what you are looking for. It is the book, The Gun Digest Book of Concealed Carry. Author is Massad Ayoob. This book (25 well spent bucks) discusses scenarios, guns, holsters, carry methods, pretty much all you need to know except for the laws in a given jurisdiction. That is your responsibility to find out, although there is some information in there. Trouble with your question is all of us will give you advice, based on our preferences and experience. And what we all would offer (10 million different opinions) may or may not work for you. Get the book, study it (it is very enjoyable to read, well written by the master himself), and you will gain a ton of expert knowledge, plenty to make your own decision with confidence. Best of luck. Oh, by the way, get a SIG 229 in 40 or 357 SIG. A personal favorite of mine, heh-heh.