I have a P365 that I carry with a TLR-6 in a Tulster IWB. I like the gun a lot, and it's been nothing but reliable. The only issue I have with it has been riding the slide stop and not locking back, but that's my fault. It does have some striker drag but I do not consider that to be a problem. The TLR-6 light sucks, but is better than nothing. Surefire just released a better light this spring. It's pricey for a 350 lumen light, but is rechargeable. The trigger is mushy, but reasonable. The trigger is probably the one place that SIG should out their efforts if they wanted to improve the gun. I probably have 1200 rounds through my gun and I shoot it really well for such a small gun despite the trigger.
If I were to do it over I would probably get the XL version for the longer barrel and the red dot capability. The longer barrel makes it ride more stable in the waist band and makes it a little more shootable. I use the 12 round mags pretty much exclusively anyway which gives me a full grip on the shorter gun. But the longer grip on the XL makes for faster reloads. If you get the XL, you can get a Tactical Development rail adapter to make a TLR-7 work on it. There are also holsters available for the gun with the better light. Originally, I was going to go back and forth between the P365 and a G19. Honestly, I think it makes more sense just to go with the XL version by itself.