As for worst places to drive, as a former trucker the following come to mind in order:

New York and surrounding area: You had BETTER be paying attention to the signage WELL in advance of the exit It's far too easy to end up on the wrong highway with no way back around. The local drivers aren't too easy on unfamiliar drivers either.

Miami, Florida: Well, it's already been mentioned in the thread, as to how bad it's laid out, and how horrible the drivers are. It's also the only place where I've ever been forced to run people off of the road to make a required exit, despite a MILE of both signalling my need AND attempting to merge only to be blocked by some idiot who doesn't want a truck in front of them.

Atlanta Georgia. Roads themselves aren't too bad. The drivers though make Texans seem laid back.

L.A. and San Fransisco. Too many cars, and rush hours capable of making saints swear. The highway system itself wasn't too bad once I got used to it. (went to L.A. alot)

Chicago: If you drive trucks, GET DIRECTIONS. Low bridges are the norm, and you don't want to get stuck under one. You MUST get directins in AND out of most freight docks there.

Most other cities fall into the general realm of tough to get around in untill you get a general idea of their systems. All large cities suffer from TMC (too many cars).