Equipment Trailer Opinion

I have a 5 ton 16 ft tilt trailer--i have moved my D2 with it but found the stopping distance with my F250 was not ideal

My personal opinion says to not even attempt to haul that D2 with your F150. You should be using at least a 3/4 or one ton, say an F450/F550 range. Your trailer would need good electric brakes or hydraulic surge brakes as well. Ability to stop is important with so much weight on. I shopped for a bumper pull Landoll tilt/stationary with winch and was floored. $23,000.00 plus taxes, and most other brands are close behind in pricing. Everything costs a LOT now. Friends have some really nice 5th wheel gooseneck units and they were close to 40K!!! Good luck on your quest for a used trailer, as they do sell fast. JM

how often are you going to move the d2, maybe contact a local tow company and have them move it 1 or 2 times a year, cheaper than a trailer and all of the liability falls on them.
get a little trailer for your tractor.
i used to move my d2 with my 3/4 ton locally / less than 10 miles, but i would not do it now because the traffic has quadrupled, and they are crazier now than ever.....
JUST MY 2 CENTS

I run a 14k trailer with a F-350, D2 is fine, a naked, early D-4 is the top limit. Good trailer brakes are a must.

In your truck manual there is a Gross Combination Weight Rating for your truck. That dictates what your max truck and trailer weight would be. Next is your drivers license and most are a standard license with a under 26K rating. Your F150 is not designed for that kind of weight....will it pull it...sure....will it stop it...doubtful. Then there are the tire ratings....the load binder ratings, chain ratings hitch ratings, etc. Lots to consider ......

I have a 2015 F-150 that I use to tow my Cat 22 weight 6,700#. My pickup with full fuel (36 gallons) and me weighs 5,760#, my trailer weighs 3,000#. That puts me at 15,460# going down the road not counting weight of hitch and tie down chains. Like Cysco said, your truck manual shows you the maximum gross weight of your towing vehicle and load. Mine is16,900#.
Another thing to consider. If you want to mount a winch to your trailer, consider getting a full tilt. Just my opinion.
Hope that helps you decide. Oh, by the way, don't expect to stop on a dime even with good trailer brakes!!
Pete

3/4 ton and 16,000# trailer - you will want to haul more than the d2. Truck then rated at 10,000# and trailer at 16,000# legal with no cdl. I run F250 6.7 with 21,000# tilt trailer rated at 16,000#. Legal load is about 12,000# +-. depending the number of people tagging along.. Just hauled D2 TRAXCAVATOR with Hyster winch over smoky mountains, never slowed down.

I use a local rock yard to have my D4 7U moved. close to14000#. Move is about 90 miles one way, $450.00 
so find it better for me to do it this way, less headaches and the cost of having my own truck and trailer,insurance etc. is out of this world now days.