This is one of the more fascinating channels that I regularly visit: Daniel Steiner
What he does is to take a map of a city and go over it in a way that peels the onion of that city's history. He's like an arhceologist just digging through layers and connecting dots that were once connected but buried or broken since then.
I am embedding two of his videos, one on LA and one for SF, to give you an idea about what he does