The top link mount on tractor has multiple holes. Are you using the one that gives you the most tilt?

 

Loading forwards backwards shouldn't matter so long as the trailer is properly supported i.e. the rear ramps or blocks in place will keep the trailer from lifting the rear of the truck. My concern here would be proper weight distribution on a short(er) trailer for the length of the load. This length will not give you much room (if any) to adjust the position of the load to get the correct 10-15% of tongue weight. That would be my concern.

 

Loading forwards backwards shouldn't matter so long as the trailer is properly supported i.e. the rear ramps or blocks in place will keep the trailer from lifting the rear of the truck.

Yes, I block the rear of the trailer when loading, not the ramps.
My home-made blocks.

 

I'm not envisioning your process. Are you using a separate tractor/loader to lift the disc as you back up the ramps? If so, that's going require some careful coordination plus how will you manage the unload at the destination?

If you are leaving the loader on the 2038, you might be able to put the disc on the trailer first with the loader, either over the side or up the ramps. Chain that down and then load the tractor. That gains you a bit of space as the loader bucket can be over the disc if needed or if you back the tractor on, it can be closer than the lift arms would allow. If you've been to a farm auction, think about how tightly packed some of the trailers leave the site.

I understand all too well the limitations of a 16' trailer. An 18' would be very nice but alas, I also have a 16 footer.

 

I was thinking of lifting the disc with front 220 loader/forks and backing on the trailer.

 

Can you back on with the disks hooked up to the 3 point? Typically a tractor hauls better backwards on a short trailer anyway.

 

This was my thought too but I have next to no towing experience.

 

Can you find a dip to put the trailer wheels in OR a ridge to back the trailer close OR even an upslope from the area where the wheels of the trailer are located, to so the ramp(s) to not have to be as steep?

Been a long time, but years ago I used to do that sort of thing to get a frequently moved lawnmower into the back of a reg cab 8ft box pickup.
This was in the days when the tailgates could be quickly and easily removed. Mower (or whatever else) could be driven up on planks. With the planks resting on the step bumper, the top of planks would be even with the floor of the bed.