I don't think you've done anything wrong, NY. You do a lot of things most never get to do. We were lucky in selling our house in Boxborough at the height of the boom. Of course, we never should have, as our house we just sold this year was 11 years of major repairs and remodeling, but it was cool and we liked it. But, if we had not impusively bought it, our other home would have been paid off long ago. I have never connected with anyone in Concord, but given the fact I only moved 9 miles (now about 6 miles, from the condo), it's all the same. I am glad my kids went to school where they did and not in Concord. Despite taking a beating on our house sale this year, we have a bit of a profit that will help us pay off the condo in a year or so. We put down almost 50%, it was the cheapest listed home in Concord except for "tear downs," and we were able to do this because DH got huge bonuses at the job he left. It was the first time we didn't have to use one of these bonuses for a home repair! We made some bad financial choices at the beginning of our marriage (well after we had kids). We took a major beating moving here from AZ, and we pretty much had to pay to get rid of our very lovely home in Tempe. It was the right choice, but it took years to get back to the type of lifestyle we had and live in the kind of town where our kids would get a good education and not be the "weird ones." It was actually harder for me than them, when we first moved here, in a place that was a perfect mismatch. There were a few years where I was teaching high school, teaching 3-7 aerobics classes a week, and teaching Hebrew School when my kids were young. We needed the money to provide them the same kind of upbringing I had... I was young, in my early 30s, but it took its toll on my health. All of my friends were stay at home moms who had been married awhile before they had kids or had family help. It was hard. I feel proud that my salary when I was teaching was enough to pay for my older son's college and his car. We wanted them to to have a clean start and no loans. Of course, he went to a state school, so that helped! My younger son felt strongly he wanted to do it on his own and that was part of his motivation for joining the military, which was weird for a kid coming from a Boston suburb. He did it himself and ended up with a full scholarship at a school that is extremely selective and has a commitment to veterans. We could not have afforded it!
I guess what I am trying to say, is that sometimes you never know what will happen. We just decided that having experiences was more important than the big house and other stuff, which was what allowed us to do all of this downsizing.