I had three TC years ago (8'/9.5'/10.5') years ago pulling various sizes of boats up to 3800 lbs when the kids were home. With many large COE lakes around boating/fishing/etc is #1 recreational activity around here. Had a hitch on the front of the truck to drive the boat to the ramp or backed it in.....which ever was easier to do.
I also made living pulling flatdeck/enclosed trailers so backing a trailer is just part of normal every day driving.
As others I've always had trailers of some type around from a small 14' tandem axle flat bed up to my present 36' tri axle 16k GN stock trailer.
We double towed with a 5th wheel RV trailer and a 3400 lb bass boat, for 8 years, bringing up the rear. No....I didn't back the combo up very far.