On the topic of less popular cities: My parents live in St. Louis. It's a wonderful place. The city was hit hard by de-industrialization, which is probably the reason why it's so affordable. It has Wash U, which is a really excellent private university. The campus is next to Forest Park and a thriving collegetown-type area. There are some gorgeous historic neighborhoods nearby as well which have been maintained over the decades, like Parkview.

The city is so affordable that it's not terribly uncommon for upper middle class folks like doctors to have vacation homes, usually lakehouses.

And I imagine there's a lot of really awesome office space available for rent in downtown at affordable rates for would-be startups; not to mention there's undoubtedly a lot of fantastic local CS talent coming out of Wash U which is largely untapped by the city.

Missouri is fully seasonal as well. It's sometimes breathtaking to see everything in bloom in the spring and early summer, and there are plenty of opportunities to play in the snow in winter.

The only thing it's lacking, of course, is an abundance of well-paying stable jobs in technology.