If I read the OP and understood it, Old Guy asked and explained the "why." Lot's of brag posts and photos - but no "why."
We all assess our local risk first. Metro vs suburban vs rural makes a difference, and that also impacts the size, capacity, and type of firearm. Add in the specific lifestyle, and then comes the corporate bans which are highly pervasive and often trump any state's permissiveness.
So the why is where you live, what you do, and how permissive the environment - then you assess not only the risk of being assaulted etc but also the risk of being "persecuted" for exercising your 2A rights in your local legal system. Detection and prosecution is a higher risk more often than actual defensive use.
I live in an Open Carry state, in a town where people can and do walk in with a gun in a holster on their hip, male and female - working retail my last OC was. Good for her. Me? Anti gun work policy, employees will be promoted to "Customer" unless you are employed at the rare inner city location where shootings have occurred. Funny how corporate policy is two faced about that. Most are, they follow the typical American pattern that they deny anyone the use of a gun until someone is killed, then it's ok to protect yourself there because it was a demonstrated threat. All too late for the victim, tho. Go figure - that's how authoritarian groups do it, tho.
BTW, does the NRA Hqs in DC allow carry? Still haven't heard about that.
So, I DON'T carry on a normal workday. Not even to and from because people break into our cars at work - small town but Metro as it is. When I am off the clock, or traveling, that's different.
Kahr CW380, because it's affordable. If used, the gun WILL be seized as evidence and I won't likely get it back for weeks, therefore I will need to have another, and quickly. I don't want to tie up $1,000 in it. Second, it's small enough - very competitive in size and weight to the LCP, which I sold. It has a much better trigger which is only another tenth of an inch longer pull that the G19 - which I sold. It has good working sights and can be upgraded if I choose, later, not rudimentary ones. At close range it might not make a difference - but if I practice at range, which is the recommended thing to do with your personal handgun, decent sights makes the experience better. It improves proficiency and helps when the situation isn't belly shooting close. When it is discharged, it's have much better recoil and handling than said LCP - it's not harshly snappy - which gets you back on target sooner. I can shoot a box of 50 thru it at a practice session where the LCP invited stopping after two magazines. Again, practice and proficiency count for more when under stress, not thinking "it's so small I can forget it's in my pocket" and never taking it to the range at all.
It has a last round hold open and it loads by the slide release - which all duty guns do. There's some points of view that it makes little difference and you should rack the slide to load any defensive gun - but that avoids the issue of loading a magazine against a closed slide. Fail to lock it securely in place and when you do rack it, they frequently fall out. That isn't better, becomes a negative just practicing at the range, and certainly will create a problem just when you already decided you needed more ammo NOW. Nope, professionals avoid weapons with no slide hold opens the same as most modern armies avoid battle rifles that have no bolt carrier hold opens. The AK and G3 are obsolete because of them, among others.
.380? Part and parcel of the improving selection of ammunition. It's not as expensive as it was a few years back, I'm breaking in the Kahr on steel cased Monarch and carrying Hornady American Gunner with XTP bullets. It holds 6 rounds but with a Mag Guts kit can expand to seven and give you a metal round follower, too. That puts the total to eight when carried loaded, again, the size and weight of an LCP if it could do that. A spare mag offers up another seven for a total of 15. If you carry a double stack pistol, will you need to have them all in the gun? Rarely. Most confrontations are handled by informing the aggressor you are armed, much less displaying it, and even less by actually shooting it, which typically involves three shots maximum. I read a lot about people justifying having a 15 shot pistol and carrying it all day - yet for the MOST part, smaller autos are selling well and getting carried. The models and popularity aren't trending toward large duty sized and high capacity guns in the last 15 years - which is exactly why Kahr started up and they are still in business making single stack smaller pistols. Even Glock noticed now that they have saturated the duty gun market and went to a single stack .380. It's their historic antecedent anyway, the Europeans were .380 duty gun users from the start of auto pistol use.
Shot placement is more important than caliber. Practice is more important than comfort. Having a gun that supports both makes it better than one that actually imposes limitations on the carrier. If you won't carry it and won't practice with it then having it becomes the issue. You might not be able to carry at all, but when you do, it should be something you will carry. A smaller, lighter gun easy to carry and easy to shoot makes a better choice.
Why did you choose to carry what you do? Pictures don't explain it.