Deck Drain Frustrations!

[Bushwacker]

That's a good idea! I had exactly that problem on port side. Maybe if you wet out the cloth with epoxy first, and then roll it up on a pencil, you can stick it up in the hole and let it kick off before you fill the hole. You can also use a center plug from the bottom like I did to create a pilot hole to help keep the angle close to original. (You'll have to go to the end of that post that I linked to in order to see the photo of the plug.)