I'm a pigtail guy too. As a trailer sailor, I just don't want one more line to rig and un-rig.
I have forgotten to hook it up before reefing, more than once, and suffered the embarrassment of the boom falling down into the cockpit when the halyard was loosed. I have also forgotten to UNhook it, more than once, but have not been knocked down as a result ... yet.
My guess is, that worst-case scenario must not happen too often, or the pigtail design would have been discontinued about 14,000 boats ago.