"The second time, Hippowdon was attempting to use Slack Off, which seems to be an obvious bad move, but apparently not one so bad that TM sees why. Gyarados shows that it has a Life Orb, but unfortunately, I do not have support for Life Orb in my log analysis function, (a shortfall that will come back to bite TM later far worse than this). This means that even though Technical Machine's Hippowdon just took nearly 50% damage from Waterfall, meaning Slack Off only wins with Leftovers recovery and risks a KO from a CH, TM still thinks Waterfall will do about 38%, making Slack Off seem like a clear winner."
If this is still the case, then it appears that it doesn't take into account the damage increase of the foe's life orb.
Anyway, very exciting to see this project advance