J.P.,
Since you are still thinking about this, i have a couple more pieces of info since i have reefed many H16s.
I can't remember what the manual says so i am wondering why you need 2 booms. The gooseneck shackle should attach to the new tack (forward reef point), The outhaul attaches to the new clew, but you should also tie a short line thru the clew around the boom to handle the mainsheet pressure. It becomes a loose footed sail. The other grommets are there to keep the excess sail from flapping around only.
Reefing a H16 is meant to be done on the beach.
A H14 sail is almost the same size as a reefed 16 sail and we used to just do that at the rental.
There was a heat at the H16 worlds in Corpus Christi in the 70s where a team reefed and won a heat. Hobie Sr. told me it was the only major 16 heat ever won while reefed. i wasn't there but have heard it was one rough event.
Most small boat sailors just figure out ways of dealing with the extra power of high wind, or they have a wind limit. As stated above the luff curve of the reefed sail doesn't match the new mast curve so sail shape suffers.
One thing to do is roll up the jib if you have like a TheMightyHobie18, or bring 3 people.