One point to think very carefully about is chafe where the towing connection leaves, so to speak, the deck of your boat. Ocean going tugs invariably use high tensile chain at the point where the bridle exits the Panama fairlead of the towed vessel. The inboard end is set up either to a Smit bracket or AKD stopper if the tow has one or it is split into several tails and each tail is made up to a set of bitts. (Tug skippers invariably prefer the former, as bitts have been known to part company with the deck!)
A yacht has a forestay and usually some sort of bow roller fairlead. It's highly advisable to include in the set up a means of lashing the towline into the fairlead very securely, and a means of reducing chafe, eg by parcelling it, or by sliding a length of very tough flexible hose over the rope before making the final splice, assuming you are not confident of your rope to chain splices - if you are, that's ideal.
I like your "round the mast and backed up by winches" idea; it is simple to tension a rope from one winch, round the mast, and back to the other winch, to spead the load.
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