Hey Weiner,
What city sucks the most for trucks to drive in?
I hate to say it because I live about 45 minutes from it but Cleveland, Ohio has some of the biggest assholes ever placed behind a wheel - they do things in spite.
I'm not a fan of the whole northeastern part of the country because things are old and not designed for big trucks.
Don't get lost in Pittsburgh in a big truck because there are waaaaay too many low bridges in that town!
Otherwise, all cities have a different "feel" to them and once you get that down - you'll be alright.