Well, perhaps it's just me...:-)
In any amount of fresh breeze, a always try to bear off when reefing or furling, and maybe try to get the headsail in the shadow of the main, if possible... I generally find heading down, instead of heading up, to be far easier, and kinder to the sail... Again, with with a good furler, fair leads and a ratchet turning block, I should have no trouble on a 40 footer in moderate conditions...
One other "cutoff point" I forgot to mention, for me... I would never, ever want to own a sailboat that required a 50 amp shorepower cord... After as many years as I have running motor yachts and sportfishermen, I am SO done with those freakin' things... :-)
And we completely LOVE the 50 amps since we live onboard. Imagine trying to heat an all electric boat in Boston during the winter without at least 50 amps!
When we had a 35 amp boat, we had to constantly balance our electric usage... gee, do we want the microwave, or the water heater, or the refrigerators / battery charger, or the washer / dryer, or the space heaters, or ......... get's quite old.
But, some people lament the use of cars instead of horses. And, some pure sailors are embarrassed to have a motor on their vessel. Some even claim a woman onboard is bad luck! Some won't rely on GPS devices. I could list the many lines in the sand which people draw for themselves, but for us, we enjoy the hot water, TVs, microwave, washer & dryer, plenty of heat, refrigerator & freezer, computers, etc., all running concurrently if we choose to. That is the American middle class way of life, and we are pleased to enjoy it.
Choose as you will.