We haven't downsized yet and are struggling a bit with the idea. So threads like this are very interesting to me.
Our house is 4500sf on 2.2 acres with a pool and a 550sf detached living space. It backs up to a 10-acre lake that we share with 8 other similar properties. Financially, we don't need to downsize, and could probably afford to hire out more of the maintenance and upkeep. But at this point, I enjoy the maintenance and remodeling projects. There's always a long list of things to do, but I enjoy the satisfaction of doing almost everything myself and learning new skills. Cleaning is a pain, but we have a fairly regimented schedule and division of chores. So that's manageable, and again, we could afford to outsource that at some point.
We truly love the property and the neighborhood, but we know the day will come when it's too much. Kids are all nearby and with their growing families, it's nice to have the space for everyone to come together for big family gatherings. We are open to downsizing and have been looking. But we have very specific requirements for the new place, so it will take quite a while to find.
Biggest issue is just the emotional attachment built up over many years of watching our kids grow up and making this place our "family" home. Deep down, it feels like the wrong decision to stay here with just the two of us. But here we sit on the patio overlooking the pool, with our coffee, while the dog chases a family of geese back into the lake.