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I'm going to have 4 reportable LSAT scores when I submit apps later this month. The first one is considerably worse than the others and there's a 2-year gap between that first score and my second administration...

Should I write an addendum about this shit? Basically, I didn't study adequately and completely underestimated the test for my first take.

Completely unnecessary. Schools will consider your highest score.

Schools will see all scores and there is no reason to draw extra attention to the lower scores. The fact that you have an upward trajectory supports that as well. No addendum needed. Good luck!