>>1573722In theory, smaller cities would be better because they're cheaper and a lower cost of living means being able to settle into a middle-class life faster. In reality, it's basically picking your poison. In smaller cities, the average wage is less than your larger cities, and opportunities tend to be more limited (so pray the city has the job field you're looking for). In larger cities, there's a better chance of finding a job in your field and the wage is higher but your cost of living is higher and most of your money will disappear to meet basic living expenses.
So, if you work in a job that pays well and could be done in Indianapolis or Iowa City, a smaller city is better. If you need to be in finance, tech, or related sectors, your best shot is moving to NYC, Chicago, SF, or LA.