Psycodog, if you're leaning towards the .380 as your carry caliber, add a Diamondback DB.380 to your Ruger and Keltec look list.
I went to a gun show to pick up a "business carry" Ruger LCP and ended up leaving with a Diamondback as it just felt like a better made gun.
My job requires khaki pants as part of our "proper attire" and I'm in a mix of neighborhoods every week so it's always on me.
Because I'm reaching, stretching, climbing, etc. inside homes, hip carry is not possible for me due to possible brandishing, so pocket carry is my work carry situation. The Diamondback disappears with an Uncle Mike's pocket holster in either my front or back Docker pocket.
They're made right here in Florida and they shoot as well as my full size HKs. I've spoken to several dealers and a lot of local LEO's have been picking them up as their back-up guns. Just another possibility.
Raptor