Yah, baby stay sounds like a better term.
Your photo shows the very long boom -- probably like Georgia's used to be. Our boom is round also, with a worm gear drive with a special winch handle for roller reefing. Now, of course, with bails on the underside of the boom for the main sheet and traveler system over the cabin house, we have to use slab reefing.
Georgia has no vents -- dorade or otherwise -- on the cabin house. The forward hatch cover at an angle is a nice wind scoop. Our climate and water temperature are cooler than yours so the extra ventilation is not needed.
I think the original main would have been too big without more headsail. Weather helm would result. Your story confirms this.
Do you have a centerboard?
I think I can see the split backstays.
We have a large window on the forward face of the cabin house. Eighth inch polycarbonate. While the polycarbonate is well secured with lots of screws, I have some concern about a large wave breaking over the bow coming aft and punching out the polycarbonate. Where the aftmost ports are, large windows have been installed. At least the window materials is 1/4 inch. Waves can be huge and steep in the Great Lakes.
Is the traveler for the jib sheets a flat brass bar? Is the bar mounted on the top of the rail? Does the bar have holes in it at regular intervals and do the cars have thumb screws that drop down in these holds to hold the car in position?
Is the afterpart of your cabin house raised compared to the level of the cabinhouse where the mast is stepped on the deck? It doesn't look like it in the photo.
Well, enough questions. Let me know if I am asking too many?