We’re thinking it through. Our basic house is fairly small to start. We added an in-law apt onto it (almost 30 yrs ago now, and fully handicap accessible). DD will be renting that (at low cost) in order to save for a house. (As you know, OP, housing costs are crazy here and it’s very hard for the younger set to cough up a down payment and absorb housing costs here today.) I’ve sometimes wondered whether it might make sense to keep our house so that we could actually use the in-law ourselves some day down the road (if one of our kids is interested in living in the main house - we will have to see). But the whole house needs decluttering, repairs, a few upgrades and ongoing yard work, snow removal, fencing, etc. We do enjoy a pool, screened porch, front porch, deck, fire pit, family room, sunroom, etc., and all of those amenities we already have here can be
hard almost impossible to find In one place if we buy elsewhere. (I look all the time.)
OTOH, I would love something smaller and newer, in an area we’d like to be, preferably a condo. But a lot will depend on where our kids wind up, as we’d like to be near them if possible. (All indications seem to point to them staying fairly local.) We plan to be involved grandparents if we’re blessed with that someday. (We had kids a little later in life so ours are still somewhat young compared to many other people our age.)
Another issue we have is our dogs. We’re dog people and will probably never be without at least one. Currently we have two. One is 9. We rescued another last year who we were told was 8. That worked, timing-wise, for us (figuring we’re not doing anything, really, for a few years). Well, we got that dog and lo and behold, he’s probably more like 3 or 4, so he’s got a longer life expectancy with us than we’d thought. (And we won’t give him up.) If we do ever get a condo, I would like one not only in the area we like, at a cost we can afford (which may work out if we sell our house), with a layout we like, and with at least a small yard for the dog(s). Not to leave dogs out there alone, but a place for them to go to the bathroom that doesn’t involve walking in the middle of the night!
I haven’t seen anyone else here mention the pet factor, but we can’t be alone in that, can we?
FL is a possibility, keeping an open mind about it. Kids might be interested, too. Another thought is possibly a condo there, but I’m not sure we’d be able to afford that unless we stay put where we are now, but that is another possibility.
I will say that, as a nurse, and taking care of my mother at home with us until she was 94, and seeing all the issues we had to deal with medically with her, my eyes are fully open to what potentially lies ahead for us as we age, so I want to make wise choices as we go forward, both for us, and for our kids. What that is, I’m not really sure. But first step we have, regardless, is decluttering, and we’re working on that. We bought a trailer for weekly dump runs and have been donating a bunch. We have a long ways to go, though, still.