That's actually a very smart question. Because the skill says, "If your Life Points drop below 1000, your coin tosses always land on heads." I would interpret this as 1)yes 2)no ;but I don't know for sure.
nah...if your life points is 1000 or higher, the skill will not activate anymore. It is auto-skill. The skill activated automatically as long your life points below 1000, and if you increase your life point 1000 or higher, it will not activate.