Does each instance of damage from Teemo Strategist count as a separate damage instance, requiring Deflect to be triggered multiple times?

Ruling: You pay for Deflect when you choose target(s). Since Deadbloom Predator is 1 target, you only pay for Deflect once, not 5 times.

Nuances:

• Blue Teemo is still widely debated and might change later
• On Void Gate, if Teemo reveals 5 hidden cards, he can deal 10 damage maximum