Vnicepeeps-
I think you have hit the nail on the head about learning from each place. I had a disaster in when I lived in Gloucester with a DIY nightmare house that I was coerced into buying, a job that was a road to nowhere and neighbours that could have been on a "Neighbours From Hell" programme. Today I took the train to Slough that was headed to Gloucester and I thought about how much I'd love to go up and see my friends, go to the farmer's market and sit in that garden I worked so hard to clear. I am so grateful for the things that time in Gloucester taught me (I wil NEVER buy a house again)--it also makes me appreciate the lovely home and town I live in now and I know my limits much more than I ever did.
I think that the biggest impact on how well we settle into a place is the community ties we make. We have it harder than some because we have to start from scratch here with making friends, getting to know the places, etc without the formal structures that childhood or university created for us to make those ties.