Instances of damage
One activation will prevent all the damage.
The number of instances of damage is the number of times the verb “to deal” is used. Pestilence's ability says “Pestilence deals 1 damage to each creature and each player” - the verb “deals” is present only once, so all that damage is simultaneous and is one instance. Damage redirection effects don't modify the number of instances of damage - they just modify the recipients. So after applying Jade Monolith's replacement effect, you're being dealt 2 damage by Pestilence. The 2 damage will be prevented by a single activation of Circle of Protection: Black.
Daniel Kitachewsky
L3, Paris, France
Rules NetRep