Great post, BR.
When learning to sail as a kid, I would never go out if a single whitecap was visible -- I was terrified of ... what ... failure, capsize, death, loss of control? Then one day my cousin talked me onto the Sunfish in 30 knots. We dumped it 15 times that afternoon, and our greatest risk of drowning was cuz we were laughing so hard. By the end of that day, we were staying mostly upright and surfing like pros. And ever after, I looked forward with mad piratical gleam to those days when you just knew the rail would be dragging all the time.
Which is not the same as recklessness, exactly. I just enjoy sailing in the upper half of a boat's limitations. Knowing those limitations (and your own) is absolutely critical to surviving on those days when you WANT a nice gentle ride but get hammered instead. Something I learned in my motorcycle days -- there's only one way to learn how far you can push before your back end unhooks, and only one way to learn how to recover from it. No matter how gingerly you ride, one day you will
break loose, and this cowboy would rather have practised for the event ahead of time.
It was alongside that philosophy I dragged our SJ21 up to a notoriously windy lake a month ago -- I wanted a chance to push it a little, see how it (and we) responded. We got our sustained 40-45 mph winds, alright. The boat was nowhere near troubled. Perfectly in hand. Kinda wish we had tested the headsail better, pushed the boat even harder; crew isn't up to snuff in that department yet. But now we can put a check in the box for "Gale, small waves, conservative tactics" and know we and the boat can manage okay. Baby steps, but I want a sense of where the edges are -- on our terms. (Now, don't even ask about my anchoring skillz.
Need practise on that.)