Probably the interarms PPK, only had the thing for about 3 months but the finish was really rough like it would cut your hand if you werent carefull while taking it appart. there was also some sort of odd wear marks on the frame from shooting it, almost like galing although it might have been from break in.
Functioned fine with ball ammo, didnt try hollowpoints but overal a rough and ugly gun, would have gladly taken your pre '68 sipow over it and gotten the feeding ramp polished, cleaned or switched out the mags to fix it, although what ammo were you using? walthers seem to really like winchester ammo.
next would be a beretta 85, functioned fine, looked okay, no jammings, trigger was great, but it has sharp serrations on the trigger that bite into your trigger finger
anyways I was cleaning under the grips and I pulled on something by accident under the right side grip and the trigger assembly unraveled on me, had to take it to a gunsmith to get the two spring one piece trigger spring back into it after failing to do it myself.
got it back, shot it for a 100 rounds and then had the thing break on me whilst practicing a safe one in the chamber, none in the magazine mag change with snap caps down in the basement where the trigger when I put my finger on it with the mag out just snapped on me and broke the spring (trigger goes slack from the mag disconnect on the 85 to begin with but it went a 100% slack all the time from it that time)
anyways it just got it back from the gunsmith this saturday with a new trigger spring, took it shooting with a 100 rounds and its functioning fine but I'm still thinking about getting rid of it and buying a German Walther PP in .380 with the trade in money.
although I think I might be to blame for it breaking since I did try to get it back together myself before giving it to the gunsmith to put it back together in the first place, meaning I could have caused a stress fracture on the spring, causing the breakage.
I really must go to the beretta forums and see what I can dig up about that since the gunsmith said that was the second one that came in with a broken spring like that but I also dont know the circumstances of the other breakage and he did say that however the 92 does not have the funky trigger spring the 85 has and it is a brand new italian made 85 by the way.
in the time it was at the gunsmith (a year, dont ask) I did buy a model 49 pre dash cop trade in to replace it and havent had any issues with that and that beretta is the first and only gun I have ever had that happen on period.