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2006 LBZ, 2009 LML, 2022 L5P. 1993 6.5 parked in the shed.
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Payload rating does not equal tongue weight rating. To give you an idea, my dually has a payload weight rating of over 5000 lbs, the tongue weight rating is only 2000 lbs.

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As to your other questions, the longer the truck the wider it turns. A long bed crew cab is a bit of an aircraft carrier as far as turning, adding a bumper pull trailer will add greatly to it. What bed length do you need to have for the boat loader that fits your boat length?

The F60 package is for things that will load the front heavy, like a camper, plow or other front heavy things, doesn't sound like you'll need it unless the boat loader is heavy (how much does it and the topper weigh?).

Wind....... that's a comfort level thing but with the boat on top, a topper, and the trailer..... you're going to find places out west like WY challenging some days. A 3500 would be better here but it will ride harsher when empty for trips into town.....would having to wait a day or 2 for wind to subside be aggravating to you?
 

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2006 LBZ, 2009 LML, 2022 L5P. 1993 6.5 parked in the shed.
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If you can, before you buy, turn all of your "assume's" into "knows" . Trucks are too much money now not to get it as close to right as you can first go. Sounds like it's going to be a cool rig馃憤.
 

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2006 LBZ, 2009 LML, 2022 L5P. 1993 6.5 parked in the shed.
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F60 would help with crosswinds from your boat being up there but will make it ride rougher. Sounds like the boat, loader, topper weight won't be any kind of real issue.

It would be nice to know what the trailer weighs empty (not it's GVWR), then you can kinda figure out what your 'stuff' would add and then have a reasonable idea of the trailer weight you would be towing.

This is a great exercise to go through and even better to be out here sharing it on the forum. You don't have to read very far around here to find folks that took the dealer or trailer dealers word on something and have ended up with bad results. Bravo to you for doing the work!

And please share pics when you get it all done, I know I said it before but this really does sound like a cool setup!
 
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2006 LBZ, 2009 LML, 2022 L5P. 1993 6.5 parked in the shed.
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If you can, test drive both lengths/configs, take them to an open parking lot and get someone to help you mark out what it does turning wise or at least watch the parking lines on the pavement to get an idea. It may not seem like much difference to some, to others its substantial. The wheelbase is what matters...and having the big battleship myself at 172" and a 160" and a 146" in other trucks....lets just say 2 of them park and go almost anywhere, one parks out back with the semi's a lot.
 
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2006 LBZ, 2009 LML, 2022 L5P. 1993 6.5 parked in the shed.
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Well that gives you an idea of what I was after. The approximate 5 feet of difference.

Ya, I kinda forgot about how hard it may be to find a dealer with a various selection on the lot......ah the good ole days.
 
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