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Hi Keith, my name is Jason
In short you would have to cut out the old transom. And laminate together a couple of sheets of marine ply with fiberglass resin until it is 2 1/4 to 2 1/2 inches thick. And then glass that in place. It's no easy feat and you would be looking at roughly 40 to 50 hours worth of work depending on how good your fiberglassing skills are. So that is what would need to be done. Did you have any other questions o the issue?
It comes down to thickness. Sterndrive transoms run 2 to 2 1/4 inch thick. Outboard transoms are 2 1/4 to 2 1/2. And if you wanted to do twins on a bracket, you really would want to be closer to 2 1/2. On top of that, it would be "rare" on a 1990's vintage boat of any make to have a 100% dry transom. Sterndrive boats tend to collect a little bit of moisture around the cutout area. And if the wood is damp in your boat (which you won't know until everything is apart) no kind of plug would stick to damp wood. Does that make sense?
To add to that, its easier and structurally stronger to get a better finish on the outside of the transom (the fiberglass skin) if you cut the old wooden core out first. The outer skin can't exacty be filled with bondo. And the correct way to do it (or the way it was taught to me and the way I make repairs) would be to get a flat piece of plywood. Wax it. Screw it to the outside of the transom. Then on the inside lay new glass down on the inside, enough so the patch pushes close to flush with that outside block of wood. When that hardens up you can pull the ply off and you will have a much smoother, and stronger surface to feather out. With a plug there isn't going to be anything to really support it.
Was there anything else?
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You are very welcome. The last thing you would want to do is spend all this time making the swap, finishing transom and making it look nice, and then 3 months down the road you see a "keyhole" type impression of the old cutout and plug on the exterior of the transom. If you replace the whole thing that can't happen. There are a few different ways to do this kind of project and so many different kinds of materials to choose from. (IE - Plywood vs Seacast vs Honeycomb cell). Skipping the exotic materials and staying with ply and polyester resin is the cheapest way to do this. You don't necessarily have to use marine ply either. Just a halfway decent looking A/B or B/C grade exterior plywood that shows 15% or less when you stick a moisture meter against it. Cost wise in materials to redo a transom in that sized boat you would be in the 400 ballpark for your wood, resin, glass, and fairing materials.
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Hello, just checking in, if there was anything else by all means feel free to ask. If not, please put through a rating on this question page. Ratings have to be done or else the website does not credit me for helping you out.