If you have a woodcore transom there is an extra measure you can take to make sure the wood is never exposed to moisture.
Align the scupper and mark the screw holes. Then drill (with a forstner bit if you have one) the holes to twice the diameter of the screws and a little deeper then the screws will penetrate. Then pack the holes with epoxy resin putty (micro-ballons or wood flour). When that cures then remark the holes and drill them to the tap size for the screws you intend to use. Then you can use a sealer that will hold the screws in place and allow removal if you break one of the plastic housings.
Its more work but you never have to worry about the chance of rot.
If the core is not wood no need to go to this trouble but I might consider a sealer that will release the screws in needed.
MD