As to question # 1 I don't know if all 20's decks sit above the stringers aft but I have found that on some of the boats that I have tore into the deck does not sit flush on the stringers but rests on an inch or so of potter putty. I assume that when building the molds for the deck they made them short on purpose so there is a margin of error when bonding the deck to hull. I would put it back together in a way that is easiest for you to do and looks good as well.
For question # 2 I recently filled my scupper drains on the 20 sceptre I am restoring and although I did not show exactly how I did it I will tell you in detail. On the underside of the boat I removed the little wedges that create a vacuum for the scuppers and threw them in the garbage. I then took my grinder and ground down 3/16" deep or so thru the gel coat and well into the glass a circle about 5 inches diameter. I then cut 3 circular pieces of 1708 each a little bigger then the last one and the last one about 4 inches in diameter. I mixed some resin and thickened it slightly with cabosil...not too thick so I could still apply the resin with a roller. By adding cabosil to the resin it makes it more sticky so the glass adheres better for up side down glassing. I then glassed in place the three pieces of 1708 putting down the smallest piece first so that the second and third piece over lapped the one preceding it by about an inch. Let that cure and then sand and quick fair over it...prime and paint. On the inside of the boat I took a wire brush that fits on a drill and reamed/cleaned out the hole because there was lots of sealant still in the hole from the original brass drains. I then took a drill fitted with a heavy duty wire brush and ground through the gel coat the entire dish or bowel what ever you want to call it so it was into the bare glass about 1/8" Clean everything with acetone especially deep into the hole. I then took some 1.5 oz matt and chopped it into small bits and mixed it with resin. Using cabosil alone is not advised as it will crack unless there is some kind of webbing to give it strength. Next I applied the matt/resin mixture into the hole and well up into the bowel of the scupper drain. The next day after everything hardened I sanded the rough stuff smooth and glassed in several layers of 1.5 oz matt so the last piece of matt is flush with the deck gutters. Quick fair over that sand and then prime and paint.
strick
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