Its based on accumulative charges and NOT the amount of times you plug the charger into the battery.
Lets say you have 1 spanking new battery with 0.0 cycles and 0% charge.
You charge to %100 on first use. This will be 1 cycle.
On your next flight, you do a quick flight and use up 30%. You full-charge your battery, Your cycle will now be 1.30 cycle.
Next flight after, you use 80% and full-charge your battery = 2.1 cycles (100%+30%+80% = 210%/100 = 2.1 cycles).
I would hate if the battery cycle count is based on the number of times you plug it in...
So in plain engrish, the P2 assist app should say 20 cycles - this is when you need to perform the 8% discharge.
In my opinion (as im no expert) - I do think the discharging to 8% will damage your battery. The discharge to 8% is to 'realign' the battery meter. I would recommend flying to 25-30% and land and ignore the discharge recommendation.