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Don't think weight is going to be your issue. Rather, physical space. I've transported a 16-G with deck and plow in a half ton pickup before. Can't imagine where I would have put a cart also. I'd advise you take a little trailer also if possible. The plows fit nicely in even a 6ft Tacoma bed and the tractors trailer nicely loaded rear first and secured with ratchet straps, so long as you don't try the Gravely 60" deck in a 5'x8'. That doesn't work mounted to a tractor. Ask me how I know...can you say two trips?
 
I needed a 6X12 trailer for my 18G with 60" deck attached.

I should be able to get by with a 5X8 for a possible addition to the family later this week :praying:

Your main concern with putting a rider in the bed of a pickup should be doing it safely. There are posts all over mtf about what has gone wrong in the process.
 
When I sold my surplus 16G, the buyer shower up in an old Isuzu PUP instead of the trailer I thought he was bringing. We removed the mower deck, and lined the tractor up behind the truck using my set of Biljax aluminum ramps left over from my rental days. I then jumped out the seat switch and walked the machine up the ramps in 1st gear low range. The weight didn't even phase the old PUP. Then his son picked up the 50" deck and put it next to the tractor- by himself. Personally, I wouldn't trust a set of folding ramps on a tractor this heavy.
 
That's a good tip, rscurtis. Takes the operator weight out of the mix too when stressing a set of ramps. Definitely take the deck off as they can get hung up even on a modest incline (say 3 ft). What I like to do is to back my truck up to my retaining wall and use a very short section of 2x10's to drive on backwards. I prefer a wide PT lumber ramp with non-skid material applied. Invaluable if you do any winter-time loading to keep from falling on your can. Ask me how I know...

Other thing about transporting one of these in a pick-up is the higher center of gravity. Personally, I don't like having all that weight up high when going down the road.

My $0.02.
 
I've hauled many a rider home in the back of a F-150 8' with two PT 2 x12s. I prefer to back them in and if I drive it in, it's scary. If a ramp breaks, all the fun is going to be over! Fortunately, most of the tractors I bring home don't run, so I have a 12 volt winch that I chain across the back of the truck bed and winch them in. Easier on the nerves, but I worry about ripping out the the "not so hard points" in my truck bed. Always something.

So I got a 6' by 12' trailer and the stress level went way down! (so did the bank account)
 
A friend of mine has one of those dlv9. It works great and appears to be built very well.
 
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