You can be as quantitative as you like, but you still have to define your preferences (aka fitness function, aka loss function).
There is really no generic advice -- some people hate winter and move to Florida or the Southwest, some people really like the change of seasons and move to the Northeast. Some people need to live near the ocean, some like mountains. Some need the high voltage of large cities, some feel better in a lower-stress pastoral setting. Etc. etc.
In practice most people are driven by job and family constraints. If you have none, well, figure out which climate zone you like, figure out whether you like large cities, figure out what do you want to do and where it's best to do it...
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Given a low (I think) fixed income and no particular local commitments (apart from citizenship in the USA) (edit: and being currently located), how do I identify a good place to live?
On further thought, since I'm in a low-density area, rather than looking for a place first it might be better to first improve my local mobility by getting a bicycle. Then I could see what possibilities it opens up, and either look for housing next or upgrade to a moped, motorcycle or car. I still don't really know where to start, though.
Edit: I tried looking for relevant ebooks on Amazon. I've found three, and from the reviews, none of them have what I'm looking for; not The Complete Idiot's Guide to Cycling (1999), Bicycling Magazine's New Cyclist Handbook (2005) or The Big Book of Bicycling (2010).
Edit 2: Every Woman's Guide to Cycling seems to have decent reviews; maybe I'll try it.