The art of sail handling and trimming takes quite some time to learn and probably a skill that may never be truely mastered.  To me, this encompasses hoisting, lowering, trimming.  Fortunately I have always sailed with a roller furl system for the jib so I have been spared some time honored "daring do", but have had the opportunity to experience more modern forms of "how the hell did we do that?" situations.  Where we have always had roller furling, we have never had our mainsail lines come aft to the cockpit so we still make trips on deck for the main and the "trash bag" sail.  We sort of learned as we went.

ALWAYS raise the main while headed into the wind.  Where this may seem like a simple theory it can make for some very interesting visual effects when it is ignored.  A downwind "Le Mans" style start is not very practical with the mainsail.  I "plead the fifth" on whether or not we had attempted this.

Because of the theory above, the reverse order makes sense for lowering the main.  Being master of the vessel, in the early days, it was my responsibility to go on deck to drop the main.  We had gotten pretty handy with this simple feat.  On one particular trip when the time came to lower main I pulled the tiller up hard, reversed course smartly into the wind, sheeted in the main to keep from getting nailed by the boom, tossed the tiller to my son-in-law and said "keep me into the wind".  The sail was flagging quite a bit in the stiff breeze.  Without another word I bound out of the cockpit headed for the mast to drop the main.  No problem!  I had done this at least a half dozen times before.  Just as I had reached the mast, the boat decided it would try to lay on it's side.  I wrapped myself around that mast like a python and commenced to scream four letter word laden commands at the helmsman.  The look of horror on my son-in-law's face was only surpassed by the death grip he had on the tiller pulled up to his chest.  I could hear things crashing below, muffled cries, my heart jack hammering, but wait.... there was something missing.....  NO ENGINE SOUNDS!  I had forgotten to start the outboard!!!!  I was being read my rights for breaking the Laws of Physics, once again.  As soon as I had turned us into the wind, we stopped, the current took over, a gust of wind hit us and away we went!  We wobbled around that point for a while until I could get back to the cockpit, drop, and start the outboard.  Sequence was everything!  (I think my son-in-law was starting to really enjoy this)