Conditional Formatting/COUNTIF help with multiple criteria

Okay, I think I stripped out all the unnecessary clutter and have the referenced formatting still in place. Please let me know if there is anything more I can explain or add!! Thank you!


EDITED: Ugh, I got so consumed with fixing the formulas i forgot to do the second part. Basically, I want to have it work so that the rule that highlights the top last name here

ex1.png

Will highlight BOTH last names, as it is referencing the 12/20 cell, and i want to have it work for all AFTER (and/or including is fine) that date, instead of just the single date.

ex2.png

Thank you!