Pathfinder and RichstillinWyo,
What I have observed is that housing is very high, and land is not affordable for a lower-middle-class class family.
Well, the housing recession didn't hit as hard here as it did in other parts of the country, so yes, land is still a little pricey. BUT we do have some of the lowest taxes in the nation! No state income tax, low sales and property taxes. And the state as a whole is pretty fiscally responsible and one of the few in the black, so they won't be riddling their constituents with tax increases to cover their butt like other places!
I've lived in 8 Wyoming towns: (Wheatland, Glendo, Douglas, Torrington, Riverton, Jackson, Sheridan and Laramie) - pretty much all over except the southwest (for good reason - stay away from Rock Springs, Evanston, Rawlins,). If you want to stay out of the wind look at Riverton, Lander, Glendo, Buffalo and Sheridan.
We live in Sheridan now, and BY FAR it's my FAVORITE place in the whole state! Well, we loved Jackson, but it was WAY too expensive and a little snooty. But Sheridan is down-home friendly, and has SO much to offer! The only bummer is housing prices, but they are dropping and the market is flooded so that will continue for a while. If you have two incomes, it shouldn't be a huge problem. And we've found that 5 acres here can support 3 horses for an entire summer! (In most parts of Wyoming they would turn it to dirt in a few weeks!)
Anyway, if your wife is in the medical field there may be a few possibilities here. We have a huge VA center, a cancer center, large hospital, 2 urgent care clinics, a couple alternative schools, WyStar treatment centers, and several elderly facilities (25% of the population is over retirement age). Just some ideas.....
As for teaching, there's the usual public schools in Sheridan, but also a couple other small schools in the surrounding towns of Ranchester and Big Horn that are within 15 minutes. Also Sheridan College and 2 or 3 alternative schools (mentined above) (Wyoming Girls School, Normative Services)
Anyway, I'd be interested to hear about your trip and your discoveries! Best wishes!