I got my first CCW permit in Seattle, in 1992. Have carried concealed in WA, OR, CA, and NV since. I'm no expert, certainly compared to some others here. But I've learned a lot since then; here are my thoughts about choice of caliber and weapon (tactics, situational awareness, etc. for another thread):
1) I believe I should carry the most firepower (stopping power + number of rounds) that I can shoot
reliably and
accurately in less-than-ideal circumstances (low light, high stress, on the ground, injured, etc.).
2) I believe that whatever I carry should be comfortable, easy to draw, easy to re-holster, and doesn't print. If it's uncomfortable and/or inconvenient, I'm less likely to carry, and I believe being unarmed is worse than being under-armed.
3) I believe it's very important to have the ability to continue engaging until a threat is neutralized -- what Clint Smith calls 'continuity of fire'.
4) I believe -- at least for me -- there is no single weapon/caliber that is perfect; anything I choose will represent a tradeoff or compromise of the above. The best I can do is choose wisely and emphasize which of these is most important to me based on climate, wardrobe, assessed threat level, and -- increasingly -- my own physical limitations.
My first carry gun was a Taurus PT92, full-size 15+1 double-stack 9mm. Terrible carry gun, but what I had. Switched to Glock 23C, mid-frame 13+1 double-stack .40SW.
For many years I thought the Glock was perfect -- relatively easy to conceal, lots of stopping power, and super-reliable. But the more I trained the more I began to realize the weakest part of my self-defense 'equipment' was me.
With 155-grain HPs, the Glock (even compensated) was pretty 'snappy'. I shot well with it, given good fundamentals, a solid grip, and -- crucial for me -- good footwork. But things fell apart fast when I had to fire while retreating, shooting one-handed or (God forbid) with my weak hand. I could hit what I was aiming at with extra focus and concentration, but I believe that a self-defense situation would likely be anything but ideal conditions.
So now I typically carry either a S&W Shield (compact single-stack 9mm, 10+1 w/mag extension) or the Ruger LCPII (subcompact .380 6+1), in kydex IWB holsters. These carry easily with my wardrobe in this climate (Las Vegas). I can shoot either of these well, with either hand, while moving. I still train about once a month; I practice one- and two-handed reloads, slap-rack-bang, and usually carry an extra magazine (partly for continuity of fire, but mostly because I believe the least reliable part of a pistol is its magazine). So far, so good.
This is what I use now, and what I think will work for me for the near future. As I get older I notice I'm losing a bit of grip strength and developing some arthritis in my dominant hand. Getting old is a b***h.

This probably isn't the ideal solution for any of you, and probably not the ideal solution for me. But after some careful consideration -- and painfully honest assessment of my own physical limitations -- I've found the
best compromise for me at the moment. I know I'll need to reassess every couple of years, and I'm good with that.
I hope some of you find this helpful as you think about which compromises are more or less important to you as you choose a weapon to suit your individual situation.