Towing a heavy trailer

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Find a truck scale or certified scale near you. It was what I did for my set up. I spent about 45 minutes. Weighed complete setup. Trailer all alone, then tongue, then just trailer on axles, and then the truck.

Having said all that, I am in the if you are towing heavy you can never have too much truck camp.
Not saying you should go crazy just saying it doesn't hurt.
 
I haul large boats with surge brake trailers. One time I lost my brakes while hauling a 6 ton Wellcraft. I was able to continue on my way without much duress to the truck, even with typical Miami traffic.
 
People forget that boats do not have the tongue weight that other trailers/travel trailers have.
Boats are usually at 10% or less.

I tow a Searay 290 that is 11,700# wet, on the scales. 760# tongue. Triple axle surge, with disc brakes on all axles.

Pushed my Suburban 2500 around a little; Ram 2500 CTD, not so much.
 
boats also don't generally have the air drag that full trailers do. It's hard to tell the comfort threshold or exactly what the OP senses is happening. Rattly-loose hitches are unsettling to me, poor shocks in the rear are unsettling, or it could be something else like under-inflated tires.
 
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