Which city?

Meh.... Depends on you. I didn't mind LA, was easy to drive but rush hour sucked. Chicago had a gazillion low bridges, New York is just all around "tight".
My hatred? Houston...

 

I would assume Chicago would top your list on Diversity, New York a close 2nd.

 

NYC, but that's my experience. yours might be different. I understand getting around Los Angeles since I was at one time from there. And Chicago is easier once you get used to it. But all of the above are terrible at rush hour. If there is any one place, I would lose it and go running naked and screaming about the curative effects of Gatorade, it would be DC......

 

The curative effects of Gatorade? I would pay to see that

 

Of those on your list, Chicago would be my least favorite. Lots of unexpected low clearances. My personal worst city to drive in is Pittsburgh PA. If you ever have the misfortune of delivering there, the reasons will be readily apparent.

Also, Chicago is the """trucking diversity""" Capitol of the world.

 

I think they train motorists of Pittsburgh how to be the worst drivers ever. Either that or something in the water supply

 

Chicago is not that bad once you get use to it. I do local runs daily in Chicago but I pull a flatbed. Up north there's a lot of low bridges even I get nervous going under them. Lot of unexpected no truck signs and narrow streets, and yes there's Chicago PD who will ticket trucks for going on that road.

 

I would say NYC. Probably the most populated and very tight streets