Didn't see this till now. My pick would have been the Sig p238 in 380 or p239 in 9mm. I have a 238 and absolutely love it, but rarely carry it. Still, smooth firearm, and one of the few autos that I'll actually carry.
My usual rotation is high standard 22 mag Derringer in shorts weather and when fishing (22 mag shotshell), Colt Detective Special for all other weather, and Colt Anaconda for open carry (legal in PA). Just my $0.02, but I vastly prefer a revolver to an automatic due to reliability and variety of ammunition selection. I handload as well, so that plays a part in it.
My other $0.02 is to spend the money and always buy quality from day one. I look at firearms with the expectations that they should unquestionably outlast me, and to buy something that is going to be the deciding factor whether you live or die when you need it.
Nobody gets all that excited when gramps gives them their old Iver Johnson or American Cycle Works revolver. It's nice, and fun to shoot, but not exactly an heirloom.
When gramps hands you his Colt Python or his Dan Wesson, or even better, his grandfathers Colt Lightning, you have it to pass on like he did.