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Living in/near a prison town isn't bad. I live in Pueblo West which almost as close to Florence as Canon City and we never have a problem. If Canon is a little too small for you, try Pueblo West or even Pueblo. Pueblo is only 30 minutes away from Canon, Pueblo West even less and they both have higher populations, more stores, etc. Colorado Springs would be pretty harsh during the winter as you'd be looking at an hour+ commute in either direction.
SheridanL - Would you be able to give advice on your impression of what it would be like for an interracial gay couple to move to the Florence area? My partner is considering accepting a job in Florence, and while we don't expect or need to be embraced by the community, we do need to feel safe. My partner is of Guyanese Indian descent, meaning he could be mistaken for being Middle Eastern, which has gotten him some unpleasant looks up in Fort Collins. We can tolerate stares and what not, but I'm trying to get an impression of whether some in the community would be outwardly hostile toward us putting down roots in the area. Any advice or speculation is much appreciated!