I am not sure what you hit when you drilled into the bottom of the transom on your 84. On my 1974 I already had a bilge drain there, and can show you pictures if you want to e-mail me. (
roger02@mts.net) When I repaired a leak around the drain housing, I did have a peek in and saw the metal housing for the de Persia self bailer. That may be what you hit, because it was not very far in, and there is not a lot of space between the bottom of the sump and the hull, perhaps an inch if that. When you see my pictures you may have a better idea of where to drill, then take another stab at it with a small pilot hole. You could then probe around with a coat hanger and get a sense of what is inside yours. It was dead center, that I know, and likely about 3/8" up from the bottom of the hull at the most.
I do know that there are stingers that extend back to the transom and you don't want to cut into those when you install inspection ports. There are a few sets of stringers. One set is about 4 or 5 inches off centerline and the second set is about 4 inches outboard of where the seat front meets the cockpit floor. These stringers are on the inside of the outer hull. There is another set of stringers attached under the cockpit itself. The first set is about 6 inches from the centerline, (just outlide the stringer on the inside of the hull) and the second set actually doubles as the side gutter to the cockpit floor. There is a third set of stringers that run under the seat part of the seats about down the middle of the seats, but that would not interfere with your plan. I can sent you these pictures, but I may as well tell you that you aren't left with a lot of room to install an inspection port between the stringers that are the bottom and the top ones that are offset from each other, and there is only (I'm guestimating) 7/8 to 1 inch between the cockpit sump floor and the hull.
I have a whole book available on the DS II if you are interested.