Me Too...
Just like Loren we too added a second opening port to the aft cabin of our 1989 E-38 inside the cockpit. Scared the hell out of me. I mean, I've drilled holes in the boat before, but this was huge!
And just like Loren I also agonized over exactly how high to put the opening. In the end I just eyeballed it based on another Ericson I had seen with three opening ports, and I just barely got the opening low enough to allow the clearance needed for the ring surrounding the port on the inside to fit on the top inside edge. So watch out that you don't position the hole too high. As for the other measurement, I decided to place the new port far enough forward to allow for a third port if we should ever need it (three opening ports were available as a factory option I believe).
The other thing I did was practice about three times on plywood, tracing the outline of the new port and cutting it out to be sure I didn't make it any larger than I needed it to be.
BUT if I read your post correctly, what Loren and we did is not what you are interested in. You want to add opening ports on the outside hull surface, right?
In that case I would say that no, I have not seen that done. I would worry that the port would be under water too much of the time, but that at least should be easy to check. Just figure roughly where the new port could fit, realizing that you need a mostly flat surface, and down low enough for there to be clearance to open the port on the inside, and try taping an outline of the port on the outside of the hull. Then go for a hard sail. If that part is under water when heeled hard on starboard tack, I would not think the port would remain water tight for long. But if it does stay high and dry, I don't see why you couldn't do it. In that case my biggest worry would be whether the hull surface matched the port well enough, that is didn't have too much curvature for the caulk to fill the gaps. I would not think that having a port there would be a structural issue.