We are now contemplating a boat that we can take back and forth from here to Wisconsin, but still keeping our slip.
Might need to get a big diesel to manage that. I'm looking at 10K pounds.
I don't know anything about renting trucks as FF suggested. There might or might not be additional insurance you'd need to purchase to cover the towing.
But as for WHAT it would require to tow something 10K plus, yes, you're looking at a 250/2500, and I'd highly recommend the turbodiesel engines. You don't need a dually, though.
My F150 is rated up to 11,500 lbs, and it works great for the amount of towing I do, on a trailer that is ~6500 lbs dry weight and ~8500 lbs - 9000 lbs wet and fully loaded. But I always recommend keeping a safety margin of 20% or more below your max tow rating.
Payload is also a consideration, some trucks have the capability to tow quite a bit, but their payloads are not sufficient. The tongue weight of the trailer, plus the weight of all gear, and all passengers, in the towing vehicle, all count against payload capacity.