My parents grew up in Milwaukee. Dad joined the army and was stationed in Alabama.
1958 - year I was born. Athens, Alabama
1959 - Fort Sill Oklahoma
~1959 (or 1960?) - Milwaukee. 2223 West Villard Avenue (Northlawn).
1966-1976 - Still Milwaukee, but parents got a house. Then dad took a voluntary job transfer to sales, his region was New England, and so family moved January of 1976. I got to stay with an aunt and uncle so I could finish HS where I had gone.
1976-2003 - Massachusetts. Milford save when in college (Amherst) and the last 8 years or so Uxbridge. What a crappy time to move. The day after I graduated HS.
2003-2008 - Dallas area, mainly Plano. Was laid off and moved to take a job.
2008-present - Bowdle, South Dakota. I won't bother to explain that one. Middle of no where. The big city, Aberdeen is 55m east (population ~25k). My house costed 26,000 (paid off) and my property taxes are 360/year so that is a whopping 30/month for the place.
So now you can scratch off South Dakota.
Best places - The house in Milwaukee for that time (kid growing up) tied with Uxbridge, MA which is a real nice town and the area has some proximity to Boston, Cape Cod, Martha's Vineyard and my favorite, the White Mountains in New Hampshire. Massachusetts is incredibly green with four seasons and awesome foliage. Of course, Wisconsin lakes blow MA away (in that regard)!
Worst - didn't care much for Dallas. Great place if you are big into consumerism. But, tennis almost year long just make sure to hold it to morning or evening during the hot days. Where I am at now isn't so hot, but at my age I don't know how I would financially handle my retirement years living in a more typical locale.