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It's not the size of the cities so much as those cities are trendy so it's hard to get a job that pays the rent.
There are cities the size of Asheville with good economies: Huntsville, AL and Lexington, KY come to mind. Lexington has a metro government so the population appears larger but the urban area is close to Asheville if that's what you had in mind.
Cookeville, TN is very small but has a booming economy. Greenville SC has a much larger metro but the downtown still has a lot of the smaller main street vibe (that's a compliment, SV). Hugely booming economy with lots of jobs.
I know this is an old thread but wanted to mention you don't always have to go to a huge city to get jobs.
Portland and Maine in general is a hard place to get a job but it gets astronomically harder on the other side of the Volvo line. I would go back to downeast Maine tomorrow if it were feasible for me to do so but I will have to wait until I retire.
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