WTH do I need to create two virtually identical rules to have multiple trigger conditions that both need to be true?

Month of "What the heck?!"
2

Be sure to vote for your own post.

This sort of “AND” logic is currently available through template triggers.. There are some limitations, however.

In your specific case, try putting the Occupancy changes to Detected for 10 seconds as the WHEN clause, and the Illuminance is below 2 for 1:00 as the AND IF clause.

EDIT: If I am understanding you correctly, the real trigger should be whether or not a person is in the room. If there is a person, then check the luminance and turn on the lights… Your current logic is reversed.