Welcome. I believe the jayflight 27bhs is a fairly long, heavy trailer? Please list the overall lengths and GVWRs for each of the trailers you have listed.
What is your payload limit from the yellow door jamb sticker on your Ford?
That's going to be your limiting factor most likely. The rigs you have listed i believe are over 30' and if i had to guess over 8k lbs. If that's so, that's likely going to be asking a lot of your truck.
Remover, from that yellow sticker payload, you deduct the weight of all passengers and cargo in/on the truck and the weight of the hitch itself, what you have left is what's available for trailer tongue weight, typically 12% of loaded trailer weights. Get please get us the GVWRs for those rigs, not the dry weights and we'll be able to help you more. Good luck