I know this is an old thread, and I don’t even have a 275 yet but I see Scout and others have the tow point on the hard top and I would want one. I have yet to grab on and shake my 200lbs on the hard top, but I don’t see why you couldn’t do it with a little modification. First I wouldn’t go through the fiberglass directly, I’d take it to a fab shop and have them weld something from the stainless side supports and come up right behind the fiberglass where the optional rod holders are like Scout does, or even through the fiberglass but not supported by it. I’ve read threads where people/kids climb up and jump off the Grady hard tops, and thinking about heavy rods in every rod holder, plus the storage up there getting pounded through rough seas, that’s a lot of leverage and weight on those tops and I don’t see a sub 200lb skier/wakeboarder pulling much harder. I’m a mechanical engineer, and the way the Grady top is supported not only like a radar arch, but supported through the metal with diagonal supports up to the windshield, I do not think you are pulling the bolts of the top through the hull since they are through bolted and not screwed in. I have a tournament 19 with a swiveleze ski pylon mounted with the base screwed into the gas tank hatch and the arms screwed in behind the rear seats and it’s pulled 250lb men slolom skiing hard enough to give you whiplash in the boat for 30 years without a single issue. My friend has an 18’ Grady with a pylon mounted to the floor hatch with the arms mounted to the stainless grab bar around the motor with a couple small extra supports that has handled the same stress. The floors and sides of a Grady are thick and solid. If the proposed skier, 200 or 250lbs of them can hang on the back of the hard top metal and bounce up and down as hard as their grip can hold, then it can hold their grip on a ski handle with maybe a couple extra welded in supports.