as a temporary fix to get you thru the summer until you can pull it apart this winter and fix it permanently/correctly? Or whats the best way to fix it in this assembled state?
For a temporary fix, I would use alum plate and silicone. I would cut a piece of aluminum plate the thickness of the transom glass or a little thinner and slightly smaller than the inside diameter of the hole (ex. 1" i.d. hole, 7/8" o.d. plug) This allows for a complete silicone seal around the plug and glass. clean and rough all surfaces of the alum plate with 40 grit sandpaper and bevel both edges at least 1/16". Then do the same to the transom on all contact areas of the plug. Bevel the edges of the transom hole at least 1/8". Mask off all surfaces you don't want scratched first. Clean sanded and prepped glass with acetone. re-mask as necessary. Next, take a block of wood or something smaller that fits into the area and covers the hole on the inside of the transom, wrap with heavy duty wax paper, plastic wrap, serran etc. and use this to back up the hole during plug installation and clamp or wedge solid in place to where you can push on it without it moving. The plastic wrap should let the block release from the silicone leaving a smooth clean finish when set. Next, using 3M -4200 silicone, place a 1/4" bead against the backing block continuously around the perimeter of the hole, then take your alum plug and push it into the wet silicone until it seats against the block and hold it there for a couple seconds until it stays put. Finally, use your finger and push/compact and smooth any remaining silicone that squezed out the surface to insure the hole is completely filled and finish as you like. Let this set undisturbed for several hours until completely dry and solid. Lastly, remove the block from the inside and your ready to go tear it up on the water again. Good luck, I hope this helps.