I would be concerned that boring a 3" hole in the transom might be like opening a pandora's box, unless you really sealed it well. An outdrive hole is a different animal because by definition, you have access to the backside, which allows for laying glass from the back to add support. In your case, only being able to access it from the outside, I think you're looking for trouble, because the backside won't be bonded to the adjacent fibeglass. It would also be difficult to waterproof the backside, unless you used epoxy putty, but then can you be sure the repair is flush and, bonded on the backside? This is why I reccomended the garboard drain plug. You can easily epoxy the 1" hole, then you have a brass receptacle that's basically designed to do the job, keep the water out or, allow for draining in the future. Of course, the only way you'll be able to get the foam out of a 1" hole is if you can disolve it. Lot's of 'ifs" here.