We've lived in the same quirky little Texas town since 1979. I doubt we'll ever leave unless the SHTF and we emigrate to Costa Rica. At some point around the mid 1990s, we discovered the best and most desirable neighborhood in town... large lots (2-3 acres), heavily treed with old-growth post oaks, natural creeks and ponds with ducks and geese, developed in the late 1960s, very large and interesting custom homes with a wide variety of architectural styles, very quiet with mostly older homeowners and few kids. From that point on, we looked at every single house that went up for sale in that neighborhood. There are only about 80-90 houses so it took us almost 10 years but we finally found our dream house. That was 2004.
We have definitely sunk some cash into this place. But we got a good deal upfront as the house needed lots of work. Still, the market value is only now approaching our cost. And we do some type of major remodel every year. This year it's the master bath. Next year, we'll redo the kitchen, which we initially remodeled in 2005. But still, these changes are mostly cosmetic. It's still a 1960s house... low ceilings, small-ish kitchen, formal dining and living, rusty old cast iron drain pipes, etc. Fixing or changing all that is not in the offing.
In the end, I think the neighborhood is why we stay. The house is a labor of love... bordering on money pit. We have four HVAC units, the newest of which is 22 years old, and they all leak freon. Don't get me started on drippy cast iron drain pipes. But I am a devout DIYer and enjoy the learning process. So for now, it's manageable and usually enjoyable.
We toy around with the idea of downsizing... smaller, modern, energy-efficient home. But we've been spoiled by this place and can never go back to a typical suburban setting. Our requirements are very specific and we've had zero luck finding anything remotely close to what we want and need. I'm a firm believer in neighborhood first, house second. So, we'll keep looking, but I would not be surprised if 10 years from now, I'm still posting about possible downsizing.