We made the choice to live in upstate New York and are putting down roots. We bought a house, I like my job and am doing well, Kevin is most likely buying a veterinary clinic, we have made really good friends. We've been able to see family a lot and make events that we wouldn't otherwise have been able to. For example, I got to go down and say goodbye to my grandfather while he was in the hospital AND be at his memorial service. That would not have been possible if we lived out West. The house that we bought, while a lot of work, does not stretch us financially (actually the opposite, we pay less than we did when we were renting a tiny two bedroom apartment) and our dual incomes go far in this low-cost of living city. It may not be surrounded by mountains or have a laid back Western vibe, but we have a lot going for us here.
Also, there is something to be said for owning your choices and being happy with what you have. I don't want to spend my life wishing I had made this different choice or that different choice. Every choice has pluses and minuses. You make your decision with the information you have and go forward. Some choices might be wrong but ultimately they will lead you to the life you are living. To be happy you need to find joy in what you have (or make a change).
While we were hiking in Montana we both kept saying we need to take advantage of what the Finger Lakes do have to offer a lot more than we have been. (And take more hiking vacations too). We made good on that the first weekend we were back and went to Watkins Glenn, a cute little town an hour and a half south of us. We hiked the gorge with some newish friends (soon to be good friends I think) and then went out to a cute restaurant for a late lunch.