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So, Olivia was bullshit.
Anorith was easy; Aerosmith 2HKO'd it with Rock Tomb and took minimal damage. Lileep however, was another story.
I planned on using Ray to take out Lileep regardless of a grass weakness, it was the only mon that could take a hit from it. Giga Drain 3HKO'd, but then it got the omni boost from Ancient Power TWICE. IN. A. ROW. I did what I could, lowered its speed with Icy Wind, but it ultimately ended in Ray's death.
Leila was my saving grace, she was able to set up with Growth on Lileep and take both it and Lycanroc out with Giga Drain. Sadly, I'm going to have to leave her in the box until I get my hands on a Sun Stone, she's at level 28, which is when it learns Quiver Dance.
Planning on using Aerosmith for the Electric trial, resisting Iron Head and immunity to Electric is sure to help out.