Which city?

For me, Philly sucks. Orlando sucks. going anywhere near Chicago sucks. and who in there right mind decided we needed a national capital anyways? I do everything possible to never go near there.
Greenbay is decent. Houston isn't bad. Fresno is decent I like Albuquerque but it gets confusing fast. pheniox ain't to bad once the ttraffic lets up.

 

On a summer day, none of those cities are too bad.

At night, when it's pouring rain, they all suck but id say going into Chicago would suck the most. It's gotta be the low clearance capital of the US. And no, your truck GPS is not gonna catch them all and it will give you false alerts.

So, when visibility sucks, crawling through Chicago in the city, has to be the worst.

 

Of all the cities listed so far, I would put Houston on top of list for traffic and forget about southern hospitality, in that traffic it doesn't exist. BTW, I'm from there. Chicago traffic sucks but is predictable and not very many low clearances. NYC is NYC and as such sucks if you're in a truck. I should add that I'm unaware of any low clearances in H-town, also LA isn't too bad once you get just a couple miles away from Long Beach and that container traffic, unless it's rush hour.
As far as diversity in drivers goes, I'd have to go with NYC. Although, I might rate Houston as #2 as it is much more diverse down there than you might think.

 

Of the list for myself, I hate new York, I've yet to go into Miami.

 

So, when you say diverse, do you mean diverse? Or dark? Because those aren't the same thing.

 

Chicago does have low bridges, but also has truck routes. I drive out of Chicago, and I have driven in New York. Chicago is easy compared to that hell hole!

 

Seattle---worst traffic because the rush hour never ends; Portland---hardest to drive in because of narrow one-way streets; Vancouver, Canada---most diversity of nationalities that seem to get along with each other

 

NYC has less snipers.

 

I disliked Miami the most off your list OP

That's part my company didn't have sun pass & I only went there maybe 10 times.

The others I've been to a bunch especially Chicago's south side.

 

Houston sucks,they don't like trk drivers and will make sure you know that.All the other cities you mentioned is my thoughts exactly.