Well this discussion had sparked my interest in understanding the laws regarding using my pickup and trailer. My interest is in being legal when hauling coal, stone, mulch, etc. for my own use. It looks like the key to it all for the typical homeowner is keeping the trailer under 10,000 lbs.
Here's Maryland's driver license classifications:

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The typical homeowner drivers license is class C and that restricts you to a trailer 10,000 lbs or less. Furthermore the 26,001 lbs restriction applied to the total combined weight, i.e. pickup plus trailer.
Tags on my trailer also restrict me to less than 10,000 lbs.
If I had a trailer that could haul more that 10,000 lbs. I would also need to get a DOT physical card. See quote from the MD motor vehicle web side:
Begin quote:
"Effective October 1, 2003, if you are a Maryland non-commercial driver operating a commercial motor vehicle in intrastate commerce (within the State of Maryland) and the vehicle weighs between 10,001 and 26,000 pounds, you are now required to hold a valid Federal Motor Carrier (DOT) physical card in your possession. If you are licensed prior to October 1, 2003, have a preexisting medical condition, and the onset was prior to 10/01/03, you will be exempt from this requirement for a 20-year period, provided your preexisting condition does not worsen. You are still required to maintain a DOT physical.
This new Maryland law, requires any non-commercial driver, operating a commercial motor vehicle that meets the conditions listed above, to obtain and to maintain a valid Federal Motor Carrier (DOT) physical card in order to remain qualified to operate a vehicle intrastate in Maryland.
If you do not hold a valid Federal Motor Carrier (DOT) physical card in your possession by October 1, 2003, you will no longer be qualified to operate the vehicle in the state of Maryland."
End Quote
My question about my load transferring hitch doesn't really help in carrying weight over 10,000 lbs. Because my tag classification isn't in the "combined" classification, i.e. towing vehicle and towed vehicle it's the exclusive weight of the trailer that matters. Bottom line keep the trailer weight under 10,000 lbs and use equipment properly rated. Requirements in your state should be similar.