"The main benefit of being part of this community is to have your assumptions challenged and to think about things from angles you may have been selectively blind to. It’s a great place to help sniff out your own biases and process things a little more thoroughly." (Malkynn)
I agree, Malkynn. I've looked for years, not been a poster, but this site has helped me immeasurably. I've come to see my biases more clearly, though overcoming them is still not simple.
Afox, barring something horrible, I'm nowhere near death, thankfully. But I hear you. My elderly parents are still in their home and won't give it up. But it's a lot for them. On one hand, given that they both grew up during the depression and are thrifty and excellent/skilled at maintenance, I think it may be helping them "stay young" by problem solving, etc. On the other hand, you can't stop aging, broken bones, bodies that will do what they do. One of the things I've realized, though, is that I'm not them. Much as I admire them, I don't get the joy or sense of satisfaction that they seem to get from homeownership/working on the home. I'd rather do my more research-oriented work, as lame as that may be.
Jrr85-- your points are absolutely what I've been vacillating on. I'm not actually in Boston, but in a bedroom community about 20 miles away. Still, prices are rising and property values keep going up. That weighs heavily on me. I like my neighbors and I am okay with the neighborhood (good things and bad things.) Friends have suggested hiring people to take care of things, which totally makes sense, especially given that it would likely come close to the additional rent. The problem is that doesn't take care of long-term anxiety. For example, we have had two "once in a generation" winters in the five years since I've owned my house, both of which required significant work/outlays of time and/or money on my part. I don't see things getting better, just more unpredictable, weather-wise.
I've contacted my old real-estate agent and am going to list it. My plan for the day actually involves re-painting all the little spots around the house where it's been nicked and dinged. It may not end up being the best financial decision and JRR85 is right: I'm likely to find new stressors renting. But for now I think it's time to try something different and honor my nerves. And next time around, I'll have the knowledge of ownership this gave me. I will have very different priorities. Thanks again, all.