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In my case, it all boiled down to the combined gross vehicle rating of both the truck and trailer. (GVWR)
In Wisconsin, the magic number was 26001 lbs. I can get the permits on line the day before I need them so that part is easy. 25 bucks a pop. I can also buy a yearly permit if needed. My pole barn is only 4 miles from the marina but just my luck, a state patrol looking for something to do, just about the time I decide to try towing without a permit.
Regarding the tow vehicle, you will get tons of advise regarding how so and so’s truck will pull just about anything. Hell with the right gearing, my Sears lawn mower will pull my boat! The deal is you want to do it safely and legally. Not sure where you are from but I would recommend you ask the proper departments for advise. Hell, I even spent a half hour at a weight station near by and got a education.
I don’t need to preach but utube is full of videos showing mishaps at launches where the boat
ends up pulling the truck in along with it. Pay attention to the ramp grade, condition, wet, slick with seaweed etc. not a good feeling when you are locked into 4 wheel backing down the ramp and you ain’t stopping. SLOW,SLOW,SLOW.