What ever you buy and carry, add a little North American Arms mini revolver in 22 mag for back up.
They are so small that you don't know they are there but they have enough stuff to them to do the job if needed.
for formal/business casual the North American 22lr derringer is the best
casual summer S&W 340pd .357 scandium
casual winter Colt CCO .45
late night high risk on foot FN 5.7
late night high risk in auto S&W 629 44 mag
7 shot taurus .357 revolver, kimber pro CDP 1911 .45 acp, CZ P0-1 9mm, Beretta Tomcat .32, 9 shot taurus .22 magnum revolver: there you go my 5 handguns of choice and for the 5 rifles: Bushmaster M4 in .223, winchester marine 1300 12 gauge shotgun, savage .22 bolt action rifle, Browning X-bolt Medallion in 7mmWSM, M&P .22 rifle
Kahr you pick the model
Glock 27
Colt commander 45
colt 1911 45
S&W J frame 38
In that order, for carry, now for shooting only 1911,1911,1911,etc.
Bill...
Some folks just make things too complicated. I like to keep it simple.
Taurus 24/7 Pro (9mm)
Taurus 709 Slim (9mm)
With those, I can do anything I need to do with a carry gun. If I need more power, I use my Marlin 1894c in .357/.38 or my Mossburg 12ga. If I need less power, I use my Ruger 10/22. No need for five pistols.