Being a former LEO, you likely have more carry experience than I do. Further, you are probably more likely to assess situations for threats and determine whether or not certain behaviors are threatening. For me, having neither law enforcement or military experience, I find that what I carry depends on what I'm doing.
If I am going to the store late at night, and then am coming straight home, I typically only carry my Glock 19 with one 15 round mag. Everything I do on the way to the store and on the way home is predetermined, not out of paranoia, but because I am more of a "routine" kind of guy. In this case, I know that if I were to need my gun, I will not likely need more than the 15 rounds because I have many different options for flight, which I'm always going to choose over a fight of any kind.
If I'm traveling more than 15-20 miles, I usually pack an extra mag with me, but again, the same situation applies. I very rarely do anything that doesn't give me the flight option. I should mention, I'm not one of those fearful people that thinks everyone is out to get me, or that I can't hold my own if need be, I'm just smart enough to realize that engaging in any hostile situation, verbally or physically, is an easy way to end up in prison or dead. People don't know how to keep things from escalating anymore, but I digress.
If I am going anywhere with someone where I feel there is a possibility for the need of a gun, which I hate doing, then I carry my .45 with 2 extra mags. The .45 being somewhere between 3 and 5 O'clock and the mags being between 7 and 9. This happens very rarely though, the first protective measure against any kind of danger is avoid a situation that could put you in danger, which is what I lot often opt for.
When I'm hiking, I usually carry either my Glock 19 or, if the weather is poor, my Ruger SBH in 44 mag. During Spring and mating season, I carry the Ruger exclusively because an angry moose is nothing to mess around with, though I've never had an encounter, and I generally only worry about 2 legged predators.
I usually have a pistol of some sort, either the Glock or one of my 1911s in the car at all times. For longer distances, especially if going somewhere I've never been, and thus don't know the neighborhoods, I will also keep a 12 gauge loaded with 6 and another 5 in the saddle.
I have considered keeping an AR in the car in the past, but it's really hard to justify that logically and legally, should I actually need to shoot at anything.