Regarding the picnic tables at the rest stop, I have no recollection about them.
I have a (still living) sister in Newcastle, Wyoming, which is on the western edge of the Black Hills. She used to teach at a rural school in South Dakota that she commuted to each day.
Mrs. Amanauensis grew up in Deadwood, South Dakota (pre-casinos). So for her, Rapid City was the big city. The place with a movie theater multiplex. The place with a shopping mall. And the place with Storybook Land (especially important to her as a young child).
I kid her, though, about the fact that she was twenty before she first rode on an escalator -- the one at the Rapid City airport. And the fact that she thought that the Rapid City Public Library was HUGE.
Anyhow, I have been racking my brain to think of some place other than Cheyenne that you and the mister could live at within year-round commuting distance. But first I have to ask -- how well do you like chili? If you love it, then Chugwater might be the place for you.