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Can an Enclosed trailer be pulled with a short box and sled deck?

I have a 8 foot deck on my short box, and am curious if I would be able to tow a V-nose enclosed trailer without taking off my deck. The trailer is a wells cargo, and obviously there would be no sleds on the deck, I know I would have to be careful with sharp turns, but I am curious to hear from anyone that has done it.
 
Sounds possible, my buddy did it with a travel trailer but forgot about the tight turns and poked a hole in the front of it lol...with the v nose I'm thinking there should be enough room, as long as there's enough space between the deck and trailer point when hooked up I'd say your good, just per check the turns.
 
I can tow my trailer with my deck. It all depends on how long your tongue is. U have to watch tight turns and pulling into driveways the angle can't be to steep. On my last trailer we pulled out of gas station and the front of the v hit the deck and put a nice dent in it.
 
Just be careful I pulled my buddies triton down with my deck on my truck didn't have any problems until I forgot it was there tried a dumb a$$ turn...not going into detail that's how stupid it was and my deck punched a hole in the trailer $400 later it was all fixed. But pulling into gas stations and everything was fine. Just remember that it's there
 
I had both a sled deck and 20' enclosed. I couldn't pull the enclosed with sleds on the deck. Wasn't able to make a turn. As someone else mentioned, I had to go with an extension that I used for my Lance camper. Worked great.
 
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