[Innsertnamehere]

Simcoe's downtown is one of the worst in the province for a town of its size. There is barely a single business of significance in the downtown - only a few banks, a small pharmacy, and a lot of very small low traffic businesses that are nothing more than bottom feeders, not key businesses.

A place like Cobourg is very clean and modern, while Simcoe is more the other side of things.

Honestly it has a lot to do with the local industry. Simcoe is US Steel and oil refineries. Cobourg is more white collar. Education rates and incomes are likely much higher in Cobourg than Simcoe, even though both are both about as far outside of the GTA.

You can't generalize across all of Canada, yet alone across all of the US. Some towns are more "sophisticated", some aren't.