Thanks everyone... I'll post an update when I have one.
So it took six months, but I do finally have an update
It was too cold most of the winter here in New England to work on this, but with the boat still shrink wrapped and on the hard, it seems like a good time to be pulling windows and vents out.
Sorry for the long long post. I do have an important question at the end concerning structure, so if anyone could skip ahead (if they don't want all the gory details) and make a comment, I would be grateful.
Today, my brother and I removed the port side deadlight. We started by removing all the screws that hold in the interior trim. Two of them had stripped heads. We used a Grab Bit (as seen on TV) to remove one of them, but the thing shattered into my face on the second. I was not happy but I still have my eyes.
Once we finally had all the screws off and the interior metal trim off, we saw that the inside metal trim really does nothing but cover uglyness.
The deadlight itself is a one piece of plastic and metal frame. The frame has the plastic sealed into it and pops in/out in one piece. There is a half inch or so flange that sits flat on the outside of the boat, and this is what needs to be beaded. So the entire assembly (less interior trim) is installed from the outside.
When I say pops out, I was being less than accurate. It was quite a bit of work. After the battle with screws was won, we had to fight a battle with the adhesives that had it sealed tight to the fiberglass. We went to a hardware store and bought a rubber mallet, a putty knife and some kind of scraper with a pointy end.
Whatever adhesive was used was pretty strong. We put the scraper in between the metal flange and the fiberglass and hammered it with the mallet, moving it along the sides of the frame. We did this all around until the flange was separated from the fiberglass. Even then it held on, as no doubt some of the adhesive got past the flange.
We finally did get the entire assembly out, leaving a nice deadlight shaped hole in the side of my boat (of course). Good thing for the shrink wrap!
I took pics of all this and I'll post them in the next day or so, after I reduce their size.
That then leads to the next question, what to do next.
Option one is to clean up the assembly and reinstall it. It seems to have been out before because it looks like there is some silicon on parts of it. The fiberglass under the flange has no evidence that there was ever anything stuck to it, which I think is odd, although I know very little about adhesives. But this gives me hope that a proper adhesive will adhere to the fiberglass. Oh, the adhesive under the flange was a yellowish brown. Much of it had tuned to a gray-brown dust.
The downside to this is that I am not certain that the leak was under the flange, as opposed to between the plastic window and the frame. I assume it was because I could see where some of the adhesive had let go, dried out and crumbled, but there could have been several leaking points. Also, its kind of ugly. Also, I am not sure I can make another adhesive stick to the fiberglass due to the possibility of silicon having been applied.
The upside is that its probably easy to do, inexpensive, and since the starboard side does not leak, its half the work.
Option two is to replace it with a flush mounted new piece of plastic, maybe smoked a bit. I read the article on doing this several times and find it pretty interesting.
The upside here is that if there is silicon on the fiberglass, a gasket material will probably still keep leaks out. Also, there is some stress cracking around the edges of the window and this could be made big enough to cover those. It would look much nicer.
Downsides are, of course, extra expense, more work (plus the other side has to be done to match) and if I screw it up it may be hard to fix. Also, the interior work seems much harder to do, although my brother (a cabinet maker) suggested that nice wooden trim could be made for the inside. He does not have the tools to do it any more, but he knows where they could be made for about $150 per side.
One concern I have involves structural integrity. When the frame is in place, it may help hold the deck up. I'm not sure. But, pushing the frame into the fiberglass hole puts the plastic window in line with the fiberglass. Bolting a plastic window to the outside may not help so much.
Any comments are welcome and appreciated, especially about the structure.