I follow him on twitter but haven't dived into his YouTube. is it worth it? I would like to learn more about transit, it overlaps some with work, but he gives the feel of Trainspotting for nerds (which is fine with me, tbh).
I have booked marked a few urban planning websites over the years that I found via Web Urbanist.
City Lab is a good one, and here's an article on the Interstate system, which I'm sure you know, was built often to divide cites (rich from poor, white from black) in the 50s' and how to repair them.
City Observatory is another one.
I don't read these blogs very much, but it's hard not to notice how the interstates have, in some cases, completely divided cities for no good reason (it's almost like they treated them as railways where, once the tracks were built, you would build a town on both sides of the tracks...but in this case the cities came first, then the interstates, not the other way around). I'm thinking Boston (rectified by the Big Dig), New Haven, Chicago...and on and on.
