Remember that ever pound of weight ; passengers and cargo ; that you load into the truck, has to be deducted from the max pin weight, and trailer weight.
The Max weights allow for only a 145 lb. driver in the truck , nothing else.
With passengers , equipment and the 5er hitch, in the truck , you'll probably have to cut the pin weight down to 3,000 lbs. to stay under the RAWR.
At 15>20% weight on the pin , for a good handling 5er.
Trailer GVWR of 15,000 > 16,500. Not much if your looking in the 35'+ range.
99DSDP 3884, Freightliner, XC, CAT 3126B, 300 HP /ALLISON 3060
2000 Caravan toad, Remco & Blue Ox.