If I conquer Monastery of Hirana with Settlement Brawler already buffed, can I choose to draw a card (spending the Settlement Brawler's buff) and then buff Settlement Brawler again with Monastery of Hirana's effect?

Ruling: Yes, you can draw a card by spending Settlement Brawler's existing buff and then buff it again with Monastery of Hirana's effect.

Sequence:

• Both "when you conquer" triggers happen simultaneously
• You choose the order to resolve them
• You can resolve Settlement Brawler's draw effect first (spending its buff), then resolve Monastery of Hirana's effect to buff Settlement Brawler again