Jim,
This is my thought on this. I hope it makes sense.O'Day cored the decks on the 272 (and many others).If the stanchion has ever leaked, the core becomes flexible. If the stanchion is flexed, the deck moves thus compromising the seal. First, I would not use silicone. Second the only correct way to fix a leak is to rebed. I would use a polysufide like 3M 4000 or 4200. third none of these sealants work well when the application is to thin. When I rebed a fitting, I counter sink the deck slightly and never let the bolt/ machine screw turn when installing. Turn the nut only and only apply the sealant between two CLEAN surfaces. If this does not work and there is still to much flex in the deck. Remove the fitting, Drill a 3/8" hole thru your old hole. Take an 8 penny finish nail and put a 90 degree bend on the last 1/4" of the point. Chuck the bent nail ( remember all the safety rules for using power tools because you are not going to use any of them here) into a dremel tool. Slowly remove the core from between the inner and outer fiberglass deck/interior liner. What you are trying to do ( Pictures are so much easier) is leave the 3/8" hole but remove the core inside the hole so that the diameter of the removed core is about 1/2 to 3/4". Tape the inside of the hole and fill the hole and core areas with epoxy. Then redrill the 1/4" hole thru the center and remount the stanchion. This solid epoxy will keep the deck from flexing at the fasteners and thus have a better seal.The rubber gasket may keep water from under the stanchion but does not seal the holes. It is the bolt hole from the outside that needs to be sealed. r.w.landaups, if there is any sign of cracking in the gelcoat around the stanchion base, do the epoxy no question.