So after 4 lost perfect nights spent troubleshooting this issue, the root cause ended up being PHD2.
I don't have a specific answer as to why it was causing this problem but switching to the internal guider ended up resolving this issue.
Full troubleshooting journey at the following:
Everything Is Not Always Great!youtu.be/_naePvzhJl0?si=Phg1nawWmjNoqtGM
and
The Most Bazaar Astrophotography Problem I've Had!!youtu.be/sB39ri8flPY?si=kQo8rCs4WuO8H9gs
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