Interesting premise. I it is marginally easier but still a fun challenge to pick ten.
1)Vieux-Québec
2)Fogo Island, to me the quintessential outport even though/because it has been touristically preserved
3)Iqaluit or better yet Pangnirtung/Grise Fiord, etc.
4)Cape Breton or PEI to encapsulate the folksy, charming East Coast
5)Hawaii though I have some reservations about whether this is actually North America
6)
Lakewood Ranch, Florida as the arch-suburban sprawl example. A Levittown for the 21st-century.
7)
Meridian, Mississippi - One of those end-of-the-line Southern cities that time and modernity have completely passed by.
8)Las Vegas - the paragon of American civilisation; monumental ambition and garishness all at once.
10)Guadalajara -Big, Latin, and cosmopolitan but also the violent heart of Mexico's drug wars.
10)Tulum - Beach resort but moreso the ruins of an ancient, advanced civilisation, the likes of which simply don't exist in Canada or the US
I struggled with swapping Hawaii for Manhattan. Hawaii is North American by ownership but not geography. Meanwhile Manhattan is probably the most iconic image of North America but I don't think it's even the best at 'Manhattanisation' anymore. I think Tokyo and Hong Kong are more interesting high-rise typographies and the skyscraper was originally from Chicago. Plus New York City has been in decline for a couple years and that is probably significantly worsening with Covid. So I've left that one off.
If we were going beyond Can-Mex-USA, I think Havana, the mountains of Jamaica, and somewhere like Tegucigalpa, Honduras would be good inclusions. I'd also swap Tulum for Tikal in Guatemala probably.