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I've towed a boat with a Ford Explorer with the towing package. It was a San Juan 23. Boat, gear, and trailer--the all-up weight was probably no more than 4,000 lbs. I'll tell you, that was a struggle for the Explorer. I surely wouldn't ever want to tow anything heavier. Most especially not around NC (I lived in Raleigh at the time), where there are lots of hills. It wasn't so bad when I lived in Florida (where everything is flat).
I would look at that 5,400 lbs. tow rating as a now-and-then, for very short trips, you don't want to do it too much! sort of rating.
For me, today, having owned a couple of trailerables, were I going to buy another trailerable, I would stick to pretty small boats--the West Wights, the small end of Catalinas or Hunters, or something similar.
Good luck!
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