There is a sweet spot between too big and expensive and too small and isolated. I have lived in NYC and there is nothing I'm missing in Omaha. Although the scale is obviously much different everything I want is within reach, and usually takes a lot less time to get to. Public transportation sucks, but it really is a great city otherwise and has some things NYC doesn't (better beers, and steaks that are better and actually affordable).
There are others within this sweet spot. Minneapolis, the less expensive bits of Denver, Kansas City, and others I am less familiar with. Omaha is pretty much the cheapest of the cities I consider acceptable, but I encourage all of you to find your sweet spot city if you want to live well or cheap.