I hate when a set up isn't right for towing. I don't dread it, but its not fun being white knuckled all the time. Thankfully it is correctable.
I dread towing in construction zones. I go out of my way to avoid them. Its not that they don't leave me enough room in the lanes, but I hate being 1 foot from a cement wall with annoying divider things sticking up, and roads that are going up and down left and right because its part shoulder part road your driving on.
Aside from that, towing isn't really a big deal. Sometimes finding a gas station in a remote town that can accomodate both truck and trailer is a pain. Or if you get turned around and you have to go miles up the road to go back another way.