Our TT is 35'. Hooked up is right at 56' overall length. I have found the only really tricky spots are fuel stops when the particular place is unfamiliar and crowded.
The tail swing is an issue to be aware off, but I'd say that anyone generally comfortable with a 20 to 24 foot trailer will find adjusting to a 35 footer will be fine with just a little time / practice.
I will say the one spot that always makes me edgy is at-grade highway crossings. Seems like when I pull up to that situation the traffic will not allow a straight shot through and the TT seems too long to stop in the middle for fear of hanging the tail out in travel lanes. I have been confronted with that and decide to make a turn and double back so that the stop in the median is at least on an angle that keeps both ends well out of the lanes.