Kyle,
Just as a reality check, that trip is about 985 miles each way. I haul tractors and other equipment around the US in conjunction with my work as a Sports Lighting Contractor. My longest trip to date was from my home in Texas to Vermont and back about 2000 miles each way. I use a D3500 Dodge one ton and a 22' utility gooseneck with ramps. I can load 10,000lb on the trailer and be legal. I roll the cost of transporting my equipment to the jobsite and back into my bids. Currently I use $1.20 per loaded mile. Because I am transporting my equipment there and back, this works for me. If I had to deadhead back as in your case (assuming you are hiring a truck trailer and driver) I would have to get $1.00 per mile for the unloaded miles. I would also have to include any toll fees and fees to cross the Border twice and a couple of nights lodging/meals.
Personally, I think your best bet is to rent a Uhaul, Ryder or Penske truck, put your tractor (it only weighs about 4000lbs) and anything else you can carry in it. Then rent a car dolly, hook it to the truck and tow the pick-up. You can load stuff in the bed and cab of the pick-up. Watch your weight!!!
I doubt you could sell your tractor for enough to buy another in Maine so unless you just want a new tractor, I would keep it and transport it.
Whether you move it yourself or you hire someone to move it for you, you can buy an insurance policy to cover damages or total loss to the tractor for a very reasonable price. Check out
Freight Insurance and Cargo Insurance-Save money and time with Ramon International
If I lived in the area, I would do it on the cheap for you just for the drive in a beautiful part of the country.
Let us know which route you take and if you don't mind sharing how about how much it cost you.
Best of luck
Tim