Retired 7 years. Turning 63 this year. Fighting the ravages of aging (and glad to remain a cancer survivor, coming up on 6 years cancer-free). With a life time interest in martial arts, I'm trying to keep everything from rusting away into obsolescence. Aging isn't for sissies, right?
Can't offer a definitive answer for someone else regarding when to lawfully CCW.
As a retired cop and firearms trainer, I'm familiar with most of the usual arguments.
I'm armed most of the time I'm away from the property. Unless one of the grand daughters are visiting (usually every weekend), I have a gun outside the safe or a lockbox.
Sure, there are times I leave the house and I'm unarmed. I have my reasons. I enjoy playing in the surf with a local grand daughter, for example (although I bought a Spyderco Salt lockblade for that purpose).
I take 1-2 LEOSA weapons when on roadtrips out-of-state. However, since one of my favorite indulgences is finding and enjoying pubs and craft breweries, my LEOSA weapons stay secured wherever we're staying while I'm out enjoying my favorite pastimes. I'm not going to hide myself away and not enjoy activities just because it's inappropriate for me to be armed.
Do I carry the same larger belt guns I used to carry in my plainclothes assignment of the last 12+ years before I retired? Not as often. Then again, in the years leading up to my retirement I'd reverted to carrying one of my 5-shot snubs off-duty much of the time. I still get out one my belt guns for those times when my activities are going to take me places where I think it prudent to have something larger than a pocket revolver or pistol, but much of the time I'm pocketing (holstered) one of my snubs or LCP's.
There are even times when I may slip one of NAA's (.22LR & a .22MAG) into a pocket holster, as either a supplemental retirement weapon ... or even as a primary "Onion Field" type weapon for those times when I don't necessarily feel like being armed in my normal manner.
Spare me the "comforting versus comfortable" lectures, as I have a passing familiarity with the reasoning involved.
I lead a more sedate lifestyle in my retirement than when I was actively working and carrying a daily caseload which took me to all manner of places where there was an increased potential for danger. I can pick and choose where and when I engage in my activities nowadays.
No, I don't have a crystal ball that can predict danger, or the lack thereof. No guarantees in life. I do, however, have some experience in making prudent risk assessments and acting accordingly.
I don't get involved in telling other guys and gals in either active LE or retirement mode when they ought to choose to be lawfully armed on their own time. Nor do I pretend to be able to make the choice for private citizens. If someone needs it and doesn't have it? Well, TANSTAAFL. There are also going to be those times when being armed may not be appropriate, or might cause issues (preventing you from entering "restricted" locations, etc).
I do it for myself, for the reasons I feel appropriate, when I feel it appropriate. Suit yourself, using whatever reasoning you feel is appropriate for your circumstances.
Whatever it is you decide to carry, though, I do recommend taking steps to remain sufficiently skilled with it (or them), and keep the ravages of age at bay, to the degree possible.
Take care.
Live long.