Regarding your question about how far away the kid would be. I'd suggest that everyone who drives practice the Quickstop. Essentially just heave-to immediately when someone goes ovbd. Whatever the point of sail, just turn through the wind, backing the headsail, then turn reverse the helm. Practice and figure out how best to execute it on your boat, especially off the wind - even with a chute up. We practiced it frequently by tossing something in the water and seeing how far away we get before the boat stops. If the helmsman reacts well, it's usually about a boat length away. Most of the time, we ended up close enough (maybe 1 boat length, 2 at the most) for my wife to jump in, swim to the kid, and for them both to swim back to the boat. All I had to do was lock the helm down, throw a floating line
out, get the ladder
down and cheer them on.
If we were slower to react or some other factors dictated, then maneuvering the boat back to them took more time and required more steps.