Would you tow this?

i know ive pulled my s185 and t250 together on a 35ft behind my 08 before. handled it pretty decent.
 
My dad used to pull his D5 on a 40ft gooseneck all the time with his 2000 3500 4x4 5spd, but it is no where near stock. He would set his cruise on 70mph and cruise on down the road.

Now he uses a Freightliner with the 8.3l Cummins and he is pissed because his pickup pulls the load better. lol

I want to say that load was well over 40k, and the truck weighed a good 10k also.

A D5 weighs just under 22k full of fluids. I just had to look one up for work to see if it could cross an area with underground facilities.
 
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