I've been where you are.... as regards pickup/trailer/tractor...need to haul, money concerns, etc.
I know it costs $$, but in the long run I'd suggest, strongly, the following:
Your current pickup is just dandy... you are on first base. Now, complement it with the right stuff.
The brake controller you have is a good critical start. You are on second base
I recommend putting a gooseneck hitch in the back of your pickup... the kind that you can remove or turn upside down when need be... so you still have a flat pickup bed for non-towing times. This moves you to third base.
Get a 18 foot lowboy trailer, gooseneck, with manual winch, wide enough for the tractor, with removable/adjustable ramps. This makes a home run.
Get 3 boomers, several tie down trucker's chains. This makes it a two run homer!
Given what you are going to be doing, all the above will be used over and over again...for many purposes. and save you money in the long run... like not having to pay to have it brought to you.... you can make the trip yourself.... and visit your benefactor....
Moving from a bumper hitch to a gooseneck increases the towing safety by a factor of 10, IMHO. Load is FAR more stable. Load balance is far less critical. You are much more able to properly load the bed of your pickup, which improves stability.
I've towed a lot of animals (lots of movement) and equipment using both bumper hitch and gooseneck pickups. Bumper hitch is always a white knuckle event, even using a 1 ton pickup, and I am always extremely tense during the entire trip. With a gooseneck, I simply worry about how to best adjust speed for up and down hills to maintain the desired reasonably constant speed... whip/sway/bounce... not a problem with gooseneck. I know it's your money... but I owe you my experience/conclusions.....
am sure that others will defend a bumper hitch with sway controller. With the 1/2 ton pickup you have, it is the gooseneck hitch that will make a huge difference in the long run....I cannot recommend it too strongly.... I would only have a Tundra if it had a gooseneck hitch.