Yes, in Massachusetts, you need a Commercial Driver's License (CDL) if you are operating a combination of vehicles where the gross vehicle weight rating (GVWR) exceeds 26,000 pounds. Since your truck has a GVWR of 26,000 pounds and the trailer has a GVWR of 10,000 pounds, the total combined weight is 36,000 pounds, which requires a CDL. Be sure to check any additional local regulations that may apply.
If the truck and trailer are not equiped with air brakes. If the truck and trailer are not comercial vehicals.
No.
A heavy duty tow truck
You wouldn't necessarily to have a commercial license, but you would still be required to have a non-CDL Class A license. Additionally, the vehicle must be clearly marked as "Not For Hire".
No
I want to be a truck driver. Is there special training involved to drive a truck with a flatbed trailer?
That combination, unless it's hauling hazardous materials, doesn't require a CDL at all. Now, if that was a 12,000 GVW trailer, then a Class A would be required. There is no such thing as an air brake endorsement - only a restriction, and only applicable to vehicles requiring a CDL.
26000 lbs of cargo? A tandem straight truck, such as a flatbed or a dump, could haul that amount of weight legally.
That would depend on the weight rating of the trailer and bridge law. For a straight truck, five to seven tons.
So long as the Gross Combination Weight Rating of the two vehicles is less than 26,001 lbs., then no.
So long as it is a commercial vehicle and the GVW of the trailer is greater than 10,000 lbs, yes. If it's hooked by a pintle and clevice, you will receive a "no tractor-trailers" restriction.
you put the quad or the dirt bike or whatever you have on a trailer or the bed of your truck and drive to the race