Oil Filter Leaking at First Prime of Oil Pump

Could be, I usually use a drill press and step up size up as I go. I never drill straight to the size unless it's 1/8 or something.

Yeah that was 10+ years ago and I was still a teenager when I tried that, I've learned a LOT since then (and broken many drill bits and ruined many holes in metal LMAO). If I did it again I'd use a drill press and work up from a smaller hole and/or step bit and take it really slow with minimal pressure.