I currently only carry one, a S&W Sigma, but my dad carries a Ruger LC9 as his smallest. Its a 9mm with a 7+1 mag count. By mom carries a S&W Bodyguard .380. My buddy has a little Beretta .32 that he carries. Another buddy has the Springfield XDS.
I used to carry a Kahr PM-40 , and thats a nice small carry piece, but now I carry a Sig P-239 its a bit larger and heavier, but I just dress around the gun to conceal it, if open carry isn't an issue then I carry a Sig P-220 . My advice is always carry the biggest gun you can, you might have to dress around it, but I believe in multiple holsters before multiple guns.
There was a time I carried a Semmerling LM-4 but I realized carrying a gun worth that much was kinda silly. Then for a while I carried a Seecamp in 32 acp, these days it is either a PF-9 or a 442 that gets the pocket carry nod.