Thanks for posting your gear list. It made for interesting reading. I've only one thing to comment on. . . .

Walther PPK/S? Where's the tuxedo and shaken vodka martini? Seriously, though, I used to have one but went to other pistols for a number of reasons. 1. It is difficult for those with low upper body strength to chamber a round. My ex-wife hated having to do so and preferred that I loaded the gun for her whenever she carried it. She preferred the much larger H&K USP (and does to this day). It's been awhile, but I suspect it may be hard to reload with one hand too. 2. The ballistics of the .380 are not up to the 9mm, .357, .40, .45, etc. 3. Given its small size, there's a lot of recoil, which can make for more difficult one-handed shooting.

I've known a number of guys who carry the PPK/S as a backup, and probably also as an "Oh S---" gun. If you can, you might want to consider something in a stronger cartridge, like the Glock 26 or 27. Just my thoughts.