I moved from Philadelphia to the Portland, ME area a few years back. My wife was relocating to work for an aerospace startup and I found a job working for an ed-tech startup. So my initial motivation to move was really for her. Aerospace is a very different field, people tend to move to where the jobs are, and the jobs tend not to be in big cities.
We ended up leaving Portland and returning to Philadelphia because both of the startups we were working for eventually ran out of capital and had leadership issues.
Why didn't we stay?
Well, we're both engineers and we both want to continue doing that for a while. There really weren't very good MechE jobs for women in Maine. So, that was a big part of it.
But we aren't entirely happy with big city life, either. Here's what we are looking for at the smaller towns we are evaluating:
1. Healthy, diverse economy. This is hard for a lot of small towns as they tend to be dominated by a single firm, institution or industry. It helps to be "on the border" or in-between a few things.
2. University or College. Having an institution of higher education nearby generally means you have access to cultural institutions (performing arts, galleries, lectures, libraries...).
3. Decent internet access. If you are going to work remote (and you're going to work remote in order to maximize your income) then you want decent internet access. A lot of smaller towns are now getting FTTH service at better prices than we are getting here in Philadelphia (home of the Comshaft). We've seen in this in Norther MN and WI, especially.
4. Within 2 or 3 hours (at minimum) of a decent sized airport. You will likely need to travel for work. Smaller, local airports are expensive and prone to cancellations.
5. Whatever other personal things you are looking for...