TractorData.com John Deere 6605 tractor information 95hp tractor, 4 foot or so wide bed of a trailer it looks like, and a metal frame drag guessing 6 to 7 feet wide. i doubt you will have issue with dragging it all. "trailer and all flipped upside down", if it is planned to run on skids. flip it over on trailer. and re chain it back down.
and yes it was late last night when replying, and very early for me this morning, so i am not all there with it just yet.
but your picture reminds me of "tractor pulling competitions" i think you have it in the bag, exception traction being only concern!
View attachment 392172
ya i just realized, it was a double axle trailer... took me a while to catch that it was double axle even after i drew in 2 wheels for one side of the trailer being upside down..
still 1600 lbs, and jumping the width / length up to what 8 to 10 feet wide and same in length it looks like. you still have a low PSI that sets on the ground. that might be good for floating it across the ground, but not much getting it to drop down into the softer dirt and move it about.
honestly i would flip that drag up side down to let it drag on the skids like you want it to, maybe add a couple extra supports to trailer, then chain drag and trailer together and then once at site flip entire thing (drag and trailer as one unit upside down) and go.