Derek, we met a while ago when you came down to Dunedin. I'm glad you finally made the move down here.
What I found very interesting is that your decisions are driven not by where to move TO, but what you're moving away FROM. Your trip to Oregon, then to Singapore and now NZ seems to follow the similar route. From a vastly different culture and super-densely-populated .sg to the extreme remote and lonesome place like .nz.
I feel that's probably not the best way to go for it. Instead of trial-and-error, how about a search algorithm? Instead of "Why am I here", why not ask "Where do I WANT to be?".
Here was the list of criteria me and my wife came up when we were drifting around for a year to look for a city to settle down.
Crucial:
1) Small country with around 5M population. Coming from China, I feel lots of the problems of modern society & politics is there because of the large degree of separation.
2) Walkabout city. We love walking. I want to make sure the walk from home to office takes no more than 30 minutes.
3) Close to nature. Tramping is our main hobby. We want to start walking in the wild with less than 1 hour drive. (Reality is the closest one is 5 minutes walk from home but that's a bonus.)
4) With a high quality university. This gives us the continuous flow of different ideas even the city is small.
5) Price is moderate. We want to have the leisure time to spend with our families and work on our hobbies. Affordable housing and reasonable prices give us the lifestyle we want without having to work our butts off.
Ok to give up:
1) Museums, galleries and fine restaurants. Even when we were living in Seattle or Boston, we spend more time on solitude activities like walking and reading. So cultural stuffs are great but we won't die if we don't have them.
2) Varieties of products/shops. We don't buy a lot of stuff and when we do, we buy ones that last very very long but not particularly in-the-fashion. So don't have much choices is not a big problem for us.
3) Weather. I love San Diego's weather. Never too cold. Never too hot. But if it's a city that rains a lot and doesn't have a proper hot summary, we're fine with that.
We visited and stayed in more than 40 cities during that year. Some we stayed 2 months, others a few days. When we started the trip, we have never heard of Dunedin. But those criteria helped us to quickly sift through the options and lead us to this unusual decision.
Three years later, we still feel grateful that we made that choice. Life is good here.
A warm welcome from Dunedin, New Zealand.