Commercial motor vehicle means any self-propelled or towed motor vehicle used on a highway in interstate commerce to transport passengers or property when the vehicle—

(1) Has a gross vehicle weight rating or gross combination weight rating, or gross vehicle weight or gross combination weight, of 4,536 kg (10,001 pounds) or more, whichever is greater;

Covered farm vehicle —

(1) Means a straight truck or articulated vehicle—

(i) Registered in a State with a license plate or other designation issued by the State of registration that allows law enforcement officials to identify it as a farm vehicle;

(ii) Operated by the owner or operator of a farm or ranch, or an employee or family member of a an owner or operator of a farm or ranch;

(iii) Used to transport agricultural commodities, livestock, machinery or supplies to or from a farm or ranch; and

(2) Meeting the requirements of paragraphs (1)(i) through (iv) of this definition:

(i) With a gross vehicle weight or gross vehicle weight rating, whichever is greater, of 26,001 pounds or less may utilize the exemptions in § 390.39 anywhere in the United States; or

(ii) With a gross vehicle weight or gross vehicle weight rating, whichever is greater, of more than 26,001 pounds may utilize the exemptions in § 390.39 anywhere in the State of registration or across State lines within 150 air miles of the farm or ranch with respect to which the vehicle is being operated.

Farm vehicle driver means a person who drives only a commercial motor vehicle that is—

(a) Controlled and operated by a farmer as a private motor carrier of property;

(b) Being used to transport either—

(2) Farm machinery, farm supplies, or both, to or from a farm;

(e) Being used within 150 air-miles of the farmer's farm.

OK, so what does all that mean?  If the truck and trailer with the tractor loaded and you and Dad in the seat weighs over 26,000 pound you need to follow all the rules. My guess is with a gooseneck you will be close.  That means commercial plates (I'm told in most states 550 miles away means farm plates = no plates if you get stopped) , CDL (you're driving a commercial vehicle interstate and not farmer exempt) , medical card (because you are interstate), DOT numbers (because you are interstate), inspection reports (needs done regardless), meet Hours OF Service and carry a proper log book. My understanding is 550 miles each way means it will take 2 days. You can't do it legally in 1 unless one of you logs into a sleeper.

 
Unless you are just wanting a grand adventure pay to have it delivered.