:: If I move the primary jib winches to the coach roof on
:: an older S22, do I need to strengthen the area on which
:: the winch mounts?

Cam I am no engineer nor did I stay at a Holiday Inn but I've drilled more than a few holes in my Santanna and not only moved the winches to the cabin top but then repositioned them at a later date. My experience is that the cabin top is very thick and if not water logged the use of area washers should be more than suffficent. Tom Fun Zone #664