I've done a ton of antique plow days with trailer type of plows.  There isn't an easy answer.  The model of plow makes a difference because while none of them back up easy some are better than others.  What I have found is the best backing plow is an IH #70 with the full castering tail wheel.  The worst I have had are the #8 IH plows.  Deere and Oliver plows are a little iffy.  You have to be really careful with Deere plows that you don't break the casting when the lock pin is in the tail wheel pivot.  Frankly the easiest thing to do is set the plow on the front of the trailer with a loader and pull it off where you are plowing and then drive on pulling the plow behind the tractor when you load on location and set the plow off with a loader before unloading the tractor.

Down in California everybody uses over head straddle carryalls easy and quick and no loading on trailers which I hate 17afarmer

If you have a full width ramp and an electric winch you can carefully pull them on backwards with the tail wheel locked.  It is just hard to keep them straight.  I thought about making a dolly to set the tail wheel in so that I wouldn't have to fight it.

Not hard to do with the D2 as long you have a tipping frailer you need the plough drawbar in a straight line with plough beams and tractor drawbar locked in the centre line it up strait and Boxbs your uncle will try and find some photos cold here at the moment about 8c today with frost tonite minus 4c

How I move my plows. I leave them unless needed elsewhere. The JD and the Case have removable hitches to pull with a pickup truck. Straddle carriers are handy for hard to move implements. JM