Alright, this is difficult.
Most displeased? My Rohrbaugh 380. But I feel I should add an explanation:
The gun works fine... now. I carry it damned near every day. However, for $1100+ it should offer SOMETHING more than the $500-$700 380s. I probably should have bought the 9mm version, but I expected more reliability out of the 380.
It took about 200-300 rounds to break it in. Before that I got every kind of jam you can think of. Now it feeds and functions reliably, feels great in the hand, and has the smoothest, most consistent trigger on any gun I have ever touched in my life.
So why am I displeased with it? Because of the price. It is a nice little gun that just isn't worth the price.
Most pleased with?
That's a tough choice, and when my RFB arrives in a week it might change, but it's a toss up between my Glock 36 and my Les Baer Premier II.
The Baer is just plain incredible. It's as accurate as you can hold it, even out to 100 yards.
The Glock 36 is simply the best carry gun I have ever had. Others on that list include a Ruger SP101, Walther P99, HK P30S, SW J Frame, and more. The G36 is a small, powerful package that works reliably and with a DeSantis Intruder holster I "forget" I'm wearing it.