Hello Buzz,
Wyoming is a great place to live. I was born and raised here and it sounds like WP was as well.
I would not recommend Casper. The population where I was born here was 18K and it still had a small town feel. It is now 55K and like a mini Denver. The benefit is, I am centrally located and can go anywhere I want within a few hours.
If I were retired and moving to the state, I would look where the housing is cheapest. Casper, Rock Springs, Gillette have a large oil and coal boom going on and it is almost impossible to even rent a place under $1500 a month. Oil is IT up here.
Cheyenne is just north Denver IMO. Anything along the I-80 corridor is wind central. I mean REALLY. Casper here averages 20mph winds over the course of a year. We see more days at 70mph + in the winter than not. 100mph is quite common here. One of the windiest states in the country.
Look in the Afton area. Star Valley is very nice. Buffalo is amazing and I would live there in a minute if decent work existed. If you want to be a bit bigger, try Sheridan. You are just a few miles from Montana and the Bighorns are your backyard.
There are many great places here, you just have to know where to look.
WM