I have no words of insight or wisdom to share; I am going through very much the very same thought processes (and the same angst) right now myself. I really like the town I live in, which is why I bought 1.5 acres and designed and built a house here in 1983 and stayed here since then. However, over those nearly 35 years, my little town has become very much "gentrified" (to my great dismay, not pride). If I sold my house, I likely could not afford to buy any place we'd even want to live in if we remained within our own town. Joining the hordes of the elderly driving around (...badly and often entirely clueless) in Florida is
not a scenario that I can imagine ever seeing in our crystal ball.
A bigger problem I'm having is really inside my own head. I designed our house myself and a lot of blood, sweat, tears and sacrifice, both physical and financial, went into constructing it. I try to tell myself now all these years later "c'mon, it's just a building with four walls and a roof and the land it sits on", but there are several decades of family history and many happy memories residing there too. There is somehow an emotional bond that I'm having great difficulty severing (at least for now). Maybe that sounds immature (or nuts), but it's the truth nonetheless. In addition, who wants to just walk away from the friends, the unique New England Yankee culture and the community of which you've been an integral part for decades? Not me, at least so far, as age 70 looms ever closer.
God willing, I've got no more than 5-8 more years (if that) of sufficient physical ability, agility and / or energy to maintain a house and grounds of this size, so it will certainly be time to "fish or cut bait" in the relatively near future. A good problem to have, I guess, still being in excellent health and with a happy and healthy family starting new families of their own, all of them happy and successful and off on their own, productively contributing to the world. Life is good!
Thanks for starting this thread Dave; I'll be watching it with great interest.