You're not the only one, we make sail shy to the main for dousing kites or rolling the jib. I'll typically hand roll a few feet of the jib (1,100 sq ft) to avoid pulling a Paris. And, if you only use one or two wraps an lightly pull when the winch is spinning you'll know immediately if anything is hung. I would never wrap 6 parts around a winch, stick it in a feeder and stomp the button. Bad things can and will happen. It's not about strength, it's about being smart with the available power.
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... :-)