For the first one, I'm going to assume "worst" to be defined as crappiest for me to shoot and not necessarily a reflection of the firearms build quality or anything like that.
I think for me that would be the LC9. I tried really hard to like it and make it work for me, but it didn't work out. The quality of the pistol itself was good, especially at the price point.
I think I would have been better off going with a PPS. I might try that again someday. I was looking for something bigger than a PM9 but smaller than a G26 (thinner) for IWB.
Worst one for reliability that I have shot - SIG Mosquito. I know, that's hardly fair, it's a .22, but compared to the Ruger SR-22 it's night and day. I would actually carry a Ruger SR-22 if it wasn't, well, a .22 and all.
Worst in terms of quality, hmm, I guess I will have to go with the Taurus 22 LR revolver we have. I mean, yeah, it's probably the least quality controlled build of anything we own, but then again it works each time, so far.