Change of route! Now I primarily use the E/W one-way canyon slope to go downstairs. It's a lot faster than taking the ladder. And I think the pirate will appear if there isn't any treasure he could possibly steal? Seems so. Although routing things that way meant 4 teleports to the well house rather than 3.

I think my execution is getting better. And I need to explore the possibility of doom strafing being a thing.