I live in upstate New York in a two-story home. My husband has a variety of physical ailments that will eventually make stairs impossible, and I've got a deep history of dementia in the family. I'm a planner by nature, while my husband likes to live life as it comes. We're both retired, and financially comfortable enough to have choices, but at some risk of outliving our resources.

Early last summer, we finally realized that we are not going to be able to age in place to the end -- our home is just not physically conducive to this. So I plunged in.

It's important to realize that every option has risks and opportunities. You can't get rid of the risks, although you can pick your exposure and try to make them as unlikely as you can. And by setting your priorities, you can make the best of your opportunities.

So, here's where we landed:
-- I've been gradually giving stuff away through our local community Buy Nothing FB page. It started with practical items we haven't used in years, or that I rediscovered by scouring the entire house to look at shelves, cabinets, closets, etc that I haven't been paying attention to. (Wow, a lot of things I'd forgotten we owned.) Eventually moved into sentimental stuff, like most of my father's sculptures. It helped to do this gradually, which let me get my head around downsizing.
-- Eventually, I decided to set up a room for stuff to keep. The goal was to make it all visible on (inexpensive plastic) shelves and also use the room very practically as a pantry, place to sort laundry, a functioning location that I was in and out of a lot. This helped me get rid of more stuff, as I realized what things I thought I would keep weren't actually going to be needed or wanted if we moved. Still working on this, because it will eventually help me decide how much storage we will actually need. This is helping me actually live in a smaller footprint right now.
-- I did not touch my husband's collections. However, over time, as he watched me do this, he started conversations about what to do with the collections that are meaningful to him. We've agreed that offsite storage is an option if he hasn't downsized his possessions by the time we move, but that he is going to give it his best shot.
-- I've been an executor twice, and yup, most of it gets thrown out in the end. It helped me start looking at our possessions through that lens. If no one is going to want it when we are gone, then why not keep only the items that will be useful, or that we cherish because we see or touch it every day?
-- One of my to-do's is going to be creating a collage (using a poster frame) of meaningful photos that could move from retirement home to assisted living to nursing home, if necessary. Most of the remaining pictures will be thrown away.
-- The more places we visited, and the more research I did, the more we refined what we were looking for. What we first thought we were going to want evolved based on experience. We spoke with our local Office of the Aging, we tried to find friends who had friends who had experience with places, we figured out that the vibe and resident culture really mattered to us, we started to understand what turned us off and turned us on. I got to know all the sales people, and compared all the contracts, and ultimately requested a copy of the resident's manual (when they say they allow pets, for example, what exactly does that mean you can/can't/must do if you have a pet, and what kind of pets?).
-- We looked into options that would give us quality of life for as long as we can, would eliminate the need to personally hire-and-fire aids or nurses (because we've eventually not going to be capable of doing that, and we wouldn't enjoy it anyway), and would make this most likely to be our last major move. This means a community with onsite cottage homes, apartments, assisted living, memory care, nursing home. It exposes us to one big financial risk, which is bankruptcy or sale of the community to someone who runs it into the ground, so we've been very picky. It also exposes us to one big social/psychological/emotional risk, which is an incompatible community, so we've been very picky there, too. It does give us the opportunity to age in a community where we can make new friends, and where one of us can move to a higher level of care and be easily visited by the other one. It also gives us lots of independence in a cottage and our own space for as long as we can make that work.
-- We're waitlisted now for three options in that community. The one we would prefer has a 3-4 year expected wait time, while the two others have shorter times, in case we need to move sooner than we hope to have to.
-- I'll be interviewing a couple of move managers and a couple of real estate agents this winter or spring, just to get a handle on possible costs, and how much work we want to do ourselves (probably not much, because neither of us are physically able to do a lot of that any more, and we don't have kids).

Basically, I turned it into a project, and by doing that, I got increasingly comfortable with the whole idea. It started out traumatizing, and now I'm actually kind of looking forward to it.

This is kind of an extreme. (It's one step short of an actual, legally chartered CCRC, which we considered but eventually rejected.) We could much more easily just sold the house and moved into an apartment somewhere, which is a perfectly viable way to go. Just wasn't our choice.