Oh, my. Not even close.
Some of these are overlapping, and I'm sure I have some of these out of order...
When I got my TX CHL, I owned a G23. Tried several holsters (IWB and Smart Carry, Pager Pal, and probably one or two others I'm forgetting).
Never could get comfortable with the brick. Eventually traded it for a G19, and then sold that.
Next came an S&W M37 (pocket carry), followed by several other j-frames (M49, M360, two M340s). Later on, I experimented with some other S&Ws...M696, M396, M325, M66, and a 3" M25. I still have several S&W revolvers, and sometimes pocket carry a 642.
At a certain point I bought a Kahr PM9. This prompted the sale of all of the j-frames. (I still have the PM9 today, and pocket carry it.)
Then I found a Kel-Tec P11. I thought...virtually the same size as the Kahr, but 11 rounds instead of 7. In theory, great idea. In practice, terrible idea. Horrible trigger, much heavier than the Kahr, and lousy reliability. After several attempts to fix it, it went (with full disclosure, at a loss). For some stupid reason, I went through three more Kel-Tecs--one each first and second gen P3ATs and a P32. I experienced similar reliability (or lack thereof) with each, albeit in varying degrees...and the same outcome as the P-11. Sold with full disclosure and at a loss.
I owned a number of 1911s, mostly 3" alloy, but three steel ones as well. Then several Commander-sized 1911s, in both steel and alloy. And one or two 5"ers as well. I do still own several 1911s, but since my last back surgery (the third) it is likely that my 1911 and N-frame carrying days are done.
I also have a Kahr P45 that I carried IWB for quite a while, and actually had a PM45 for a while.
More recently, I have bought and sold two LCPs. Super easy to carry, and both worked perfectly, but I have some lingering doubts about the cartridge.
Not sure I am done, yet...I've been eyeballing the Kimber Solo, and on occasion, the Boberg and the Rohrbaugh.