Very nice write up which should be very helpful to all reading it.
It is always easy to armchair comment on such reports, and I mean no disrespect here, but I would suggest that you have pointed towards one of my key issues with some older designs. On any small cruising boat (meaning less than about 50 feet) I am a big believer in having the main halyard and both reefs run back to the cockpit, rigged and ready to go at all times when you are cruising with a smallish crew.
With a two line reefing system for each reef, rigged properly you should be able reef the mainsail quickly and on the fly on almost all points of sail and end up with good sail shape. The ability to reef on the fly from the cockpit rather than have to bash into the wave train or go on deck is a seriously important safety feature. There are times when reefing quickly is the only safe choice, and going on deck to do is taking unnecessary chances, not just with your safety but that of the whole crew.
Depending on the design of the boat, idea of just flying the jib in heavy winds has its own hazards. In heavy winds, the induced lee helm can prevent you from safely heading up and being able to reduce sail.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay