I am allowed to carry 3 handguns on my CCW permit:
My primary carry weapon is a SIG 229 .40S&W with XS 24/7 Big Dot sights. I carry this in a Milt Sparks Versa Max II holster and Milt Sparks belt.
My secondary weapon is a Glock Model 30 .45ACP, also with XS 24/7 Big Dot sights, and also carried in a Versa Max II.
My third weapon is... a J-frame! (what else did you expect?).
It seems that everyone who has a CCW has a S&W J-frame in the repertoire somewhere.
I carry a S&W 340PD .38/.357MAG when I need something a little more concealable. I have an Inside-the-Pocket holster that makes this gun practically disappear, and I also have a Milt Sparks Summer Special II IWB holster that conceals with just a T-shirt.
The only advise I can give is that whatever you decide to carry, get a good GUNBELT to carry your holster on; a good gunbelt is the foundation that everything else rides on.
I've seen plenty of posts on THR where people complain of "holster migration" and just plain discomfort with the rigs they use. Do yourself a favor and actually put a little bit of money into what you're going to use to carry your gun in.
A cheesy leather dress belt is not adequate for the job. Most gunbelts are made of double-thickness leather and are sized with the holster to function as a unit.
Check out Milt Sparks web site to see some great products.
http://www.miltsparks.com/