I was under the impression that Bail Enforcement/Fugative Recovery (AKA Bounty Hunting)was Illegal in MA???? Hence if so I think it would be safe to say that the transporting of a prisoner would fall into the DoNOT do list.
I know states like NH,CT regulate and license Bounty Hunters but not sure about MA, like I said I thought it was ILLEGAL, but I cant remember where I heard that so I could be wrong here.