Maybe you need to create a spread sheet with all the variables and note down all the areas you discover.
From a personal perspective here are some of the considerations I would look for;
- town size
- types of work available
- type of work I want
- snow etc
- no regulations applicable
- quality of access I want
- potable
water yes / no
- neighbours storing stuff yes / no
- neighbours who also dont want restrictions or bylaws yes / no
- Can I live near them
- services yes / no
- Do I want a community
- Is there one
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