Shorter Answer: My hands have aged-out of wanting to try new concealed-carry-oriented compact guns, and my retiree’s budget is not ideal for accommodating the thousands of rounds that I would want to fire, in order to develop unconscious competence with a new system. The last time I adopted a totally new-to-me pistol system was in 2002, and that was when I had to choose a new duty pistol, from among four choices. My beloved 1911 duty pistols, which were “grandfathered” under the older firearms rules, were not working well with the then-mandated duty holster, so, I reluctantly transitioned to the Gen3 G22, for police duty, and added G27 and G29 pistols for back-up and personal carry. (In actual practice, I tended to carry revolvers during personal time, rather than the Glocks.) After a couple of years of being disappointed with my accuracy potential, with Glocks, I discovered that there was an optional trigger available for SIG pistols, that enabled me to get “enough finger” on the face of a double-column-mag SIG. I’d had prior experience with the SIG P220, which I had liked. So, I got away from Glocks, for a number of years, but eventually returned to the Glock system.
Notably, Gen4 and Gen5 Glocks fit me better, resulting in better accuracy potential than when I was using Gen3 pistols, during my first go-‘round with Glock.
Longer Answer: My last totally voluntary switch/change/transition, to a totally new pistol, though not a new system/platform, was to the SIG P229 DAK, in 2004. While I was somewhat constrained by the weapon policies of the PD which employed me, I really liked the P229. The SIG P229 grip shape fit my hands better than the Gen3 .40 Glocks I had been using, and the SIG’s slide protrudes less to the rear, which improved concealability, compared to the blockier Glocks. I’d used an old-school P220, 1991-1993, for both duty and personal carry, so, I was not unacquainted with the SIG platform, but, the wider grip frame, the optional slim factory trigger, and the DAK trigger system, represented a substantially different weapon. Notably, DAK was my personal preference. Most of my colleagues, who opted for SIG, were using DA/SA.
I gradually started reverting to Glocks, though 9mm Glocks, this time ‘round, in 2012/2013, for “orthopedic” reasons. I wanted to step-down from .40 S&W, and and use a weapon with a lower bore axis than my SIG P229, .40 S&W duty pistol. I had to keep using the SIG as long as I was assigned to uniformed patrol, but, could apply for an investigative role, which would enable me to use a Glock G19 as a duty pistol. First, I bought a pre-owned Gen3 G17, to make sure that a 9mm Glock would be noticeably easier on my aging hands. Then, I bought two “blue label” Gen4 G19 pistols, after discovering that the Gen4 was a noticeably better fit, in my hands. In September 2015, my then-chief OK’ed 9mm to be an alternative duty cartridge for uniformed patrol, so, I immediately bought a “blue label” Gen4 G17, which became my duty pistol, and often my personal-time carry gun, too.
I have, since then, added more Gen4 and Gen5 Glocks. I retired from LEO-ing in 2018, so, all handgun carry is now “off the clock.” In the absence of any such thing as department policy, I could adopt a totally new handgun system, for carry, if I chose, but 9mm Glocks continue to make sense, for carry, some of the time. I do not always carry Glocks. I still carry 1911 pistols, occasionally. A 1911 was my very first handgun purchase, at age 21, in late 1982 or early 1983, largely because I was a history buff, with much interest in the World Wars and subsequent conflicts during the Cold War. I have added some revolvers, recently, too, though no new “platforms” that I had not already been using for a number of years. My handgun I am most likely to carry, these days, is a K-Frame S&W snub-gun, not unlike one that I ordered while attending a police academy, in late 1983.
In case the above makes me seem like I do not like trying new pistols, well, I did plenty of wild experimenting and switching, in the Eighties and Nineties. By the late Nineties, when I was in my late Thirties, I was settling-down, and might well have finished my days, using 1911 pistols for duty and some personal-time carry, and DA revolvers for just about everything else, supplemented by the occasional pocket pistol for special purposes.
Notably, this is all about carry guns. Collecting is a separate hobby. I do not feel a need to carry my collectible firearms.