deckover vs lowboy for skid steer?

/ deckover vs lowboy for skid steer? #11  
My only concern is making it between the gates at the entrance to my driveway. I live on a 2 lane country road with a ditch directly across from my driveway. I could make it in with a tandem axle dump pulling a 30' trailer with a backhoe yet I have to jack knife my trailer to make it in with a 20 + 5 GN setup. Being that I'm over the limit on that trailer with some of my equipment, it's reeeeeally hard on it to twist it that hard to make the turn since it's a tandem axle but not dual wheel trailer. I'm hoping a 30' pintle hitch with tandem duals will do the trick.
 
/ deckover vs lowboy for skid steer? #13  

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