Years ago I had a boat, Bearcat outboard & trailer that I towed with a Mustang II. I did 2 things that impacted my towing. Switching to a Pinto as the tow vehicle made it more difficult. It was an 18 foot trailer, mostly 'tongue' and I only had a 14 foot boat (it was about 1300 lbs load, plus the galvanized trailer). But what I did that seemed good but was really bad was, since the boat was short I cut the tongue part of the trailer to make it more maneuverable. I didn't realize that when I used my brakes the dynamic tongue weight could be enough to make the Pinto do a wheelie even while braking.
Luckily I am a conservative driver (all the trucking DNA) and when I started to lose my steering I eased up on the brakes and managed to avoid hitting anything.
I honestly can't remember even considering the towing capacity of the cars or the hitches, but I think they were 2000 lbs too, being the early 80's they hadn't started using the 1 inch receivers yet AFAIK.