Big 4 states

[Santander]

1. New York (only because it has NYC and Buffalo, otherwise it would probably be my last choice as the state outside of those 2 cities is essentially one big dump with high taxes to top that off)

Buffalo is a dump.

Source: Lived in Niagara County (which is far nicer than Buffalo)

New York would be #1 for me, but for the Adirondacks and not Western NY.

[Santander]

1. Key West
2. San Luis Obispo
3. Albany/Schenectady/Saratoga Springs
4. Who care

That's your list? Really? Like, knowing what you like, I'm sure you'd prefer California's Central Coast to Key West (but it has much better towns than SLO) and the Hudson Valley is much more charming than Albany. Come to think of it, California is the best-fit state in the country for you but actually--climate, landscape, food, Catholicism--it's all here.  

Central Coast and the Capital Region are excellent choices. Key West is strange, but Florida sucks anyway.