The loader in the air like that would make me a little uneasy especially considering the grapple weighs a good 500lbs or more. The loader arms are equally as heavy.If my measurements are correct, the tractor and bush hog will have about 2" of clearance when I fold up the tailgate on the 16' trailer. I'll have to lay the loader up on the headrest like in the pictures and fold up the tail wheel on the mower to do it, but that seems pretty easy.
Consider modifying the trailer so that the bush hog wheel goes over your front box. Did you get your tires filled? Not sure if you have brakes on the trailer, but keep your total weight in mind if not.
2,700lbs - 3800
700lbs - Loaded R4s
800lbs - FEL
500lbs - Grapple
620lbs - RCR2060
= 5,300+ Pounds PLUS the weight of the trailer.