I have the S&W 380EZ, Ruger Security 380 Lite Rack, Walther CCP M2 380 and also the Ruger LCP II Lite Rack 22lr. Here are the raw facts you need.
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The pistols are S&W Shield 2.0 9mm, S&W 380EZ. Walther CCP M2 380, Ruger Security 380 and Ruger LCP II Lite Rack 22lr.
Experiences:
The 380EZ has that grip safety that has to be held in.The magazines have little stubs on the follower like many 22 magazines.
The Walther CCP is the most difficult to reassemble and you need to pull the trigger with an empty magazine to field strip but it was the most accurate of all since it is a fixed barrel. It uses a piston to delay the slide so it is soft shooting like the others. If you try to stage the trigger it is perhaps the worst trigger in the group but if you simply pull smoothly straight through it might be the best.
The Ruger Security 380 is a staggered stack magazine and so the grip is slightly wider which might make it the most comfortable. It also comes with a green fiber optic front sight that's very easy too pick up. Add in 10 and 15 round mags and it certainly should be considered.
The little Ruger LCP II 22lr might be the ideal though. Once broken in it is very ammo forgiving even shoots bulk stuff relatively reliably. It still won't fire total dud rounds but with the really light rack that's less of an issue than in the past. It comes with an aid for loading magazines that's really easy to use. Also it has the lowest felt recoil of all but surprisingly, not by much. The three .380s are really really soft and gentle shooting.
All the measurements are the average of five pulls using my Lyman Digital Scale.
I also have the Beretta and Taurus tip up barrel models but can't recommend them. The issue is failure drills. If you get a light strike or dud you need to remove the carcass manually. That means tipping the barrel up and if the dud doesn't fly out digging it out with your fingers. Neither of them have an extractor and the slide is tiny and springs very heavy.