Dunno what the answer is, but we're boomers (very late). Our house is too big for us and we're willing to downsize, but there's nothing in our area that works for us. We're unwilling to buy a much smaller house for much MORE than we paid for this one. Well, we would, but most of them are overpriced junk. In CA, we can roll our tax base over three times, so it isn't really the taxes. We have no mortgage, so it isn't really the interest rates. There is literally nothing to buy. We've been actively hunting for our next property for five years.
We look at open houses regularly, then follow up to see what they sold for. Yesterday, two in the recent cohort went for $200k over asking, oof. As long as demand exceeds supply, it's probably going to stay this way.
Sidebar: Our kids live in an area that has a strong employee housing program. Problem is that older people's kids grow up and move on while the parents stay in their cost-controlled home. Worse, the parents retire and then they're technically not even employees. This makes it tough for young families. So the housing board (I'm deliberately being a little vague here) has been actively working to downsize older people from their large homes. Our kids just bought a right-size home for their family of five. The housing board gave the previous owner, now a widower, $100k and the opportunity to buy a brand-new, right-size for one, home for less than the value of their existing home.