Great responses so far. Lots to think about.
Answering my own question, obviously your outlook is going to depend on your personal situation. I'm retired, debt-free, and live in a safe environment. There is an extremely low probability we will need to repel boarders, unless the mob can make it over the Tampa Rocky Point causeway (3 miles), past the gates to our complext, and back to our apartment. Nevertheless, we are exploring other locales, both with an eye for reducing financial burden (we live in Hillsborough County, the highest sales tax rate in FL), better weather (FL is hot year round, but unbearable Jun/Jul/Aug. It's 96F right now on my porch.) Our upcoming trip out West is partly for this reason (but mostly to get away from the fricken' heat.)
I'm focusing on the things that have the biggest impact on my health, and bang for the buck. Meaning first, dealing with creeping belly fat and diet. Meaning, no shit dropping the 30 pounds that's seemingly come out of nowhere (which, of course, it hasn't. You don't frequently have a medium rare rib eye with sauce bernaise and a bottle of Merlot without consequences.) And adding a regular routine of exercise, both cardo and weights. I'm about 8 days into that program. I feel like I can sustain this.
On the gear side, I'm in the middle of a transition from Glocks to Sigs. I have traded my 10 round G43X EDC for a 12 round P365XL. That gun is still being vetted. I still have my G19 for USPSA. I'm waiting for a range/competition holster for the P365XL, as well as two EDC (one from JM CK, one from RCS) holsters. Once I complete that transition (assuming I do) I will likely trade the G19 for another P365XL. And finally have the 'two guns, one for training, one for EDC, that I should have done in 2014 when I started shooting. Once thing I probably will do is get a couple 10 round mags for the P365XL, in the event of a mag ban above 10 rounds. This consideration drove me to a P30SK in 2016, ahead of the election. While that combo (VP9 for USPSA, P30SK LEM for EDC) didn't work, really, I think the P365XL might be that "do everything" gun, for me. I should add we also have a 10 round P365, which is shootin partner's gun.
On the ammo side, I'm going to look at my consumption last three years, average it out, then buy enough to be set for 4 years of my expected use (training class 2x a year, matches at once per month, square range occasionally).
Otherwise I don't see much in the way of new gear needing to be bought. I don't do long guns because: reasons so I have no need to get into a pump or AR. Investment wise, we're invested in the market, and have a modest retirement plan. Medical we are on a post retirement COBRA plan, but be looking at Medicare at some point, reducing our monthly outlay.