Mikey and Suprahunter i agree with you both 100% you should drill from the Gel Coat side and counter sink holes.

The front legs of the tower are actualy not under that much stress when pulling a boarder. The Rear legs are taking the brint of the force.

As i said before if you use small bits and progresivly get bigger you wont have any issues.

I can say i have drilled about 13 new holes in my boat in the gell coat. I have seen exactly what happens when you drill, cut, heat, sand and file gel coat on these boats. As long as your going small and getting bigger, going in reverse so the bit doesnt bite into the gell you can go threw from the back side and not cause splinter cracks.

Its never recomended but it is possible. Taking the tower off is the best option but it wasnt and isnt always an option for everyone. I can also tell you stereo shops Do Not remove your tower when they run speaker wires as a normal practise. They drill it from the inside out and i would bet money they dont step up the bits from small to large.