Since it is so easy to adjust your tongue weight I have never seen seen the need for a load leveling hitch, on the other hand, if you are towing something like a travel trailer they are a must. A lot of people are now pulling small travel trailers with SUV's and it is scary how many don't use leveling hitches
Kioti CK3510SE HST, Ford 3400, Gizmow ZTR, Simplicity 7016H
Depends on if he is gonna carry a heavier load than his current tractor or not.. A gooseneck trailer really works wonders for keeping your tow vehicle more level and safer.. not to mention the much, much better maneuverability..
I would just add use 4 tie downs, one at each corner of the tractor. Myself and many others on this forum have seen so many people hauling stuff without any tie downs or poor ones. It seems like in my area, people that cut grass for a living have special trailers and equipment that don't need tie downs. Don't fall into the "I'm only going a little ways so I don't need to tie it down" frame of thinking.
Otherwise it sounds like you have a good trailer and rig for what you will be doing.