Listen kids, don't stay up past your bedtime trying to troubleshoot something, it's likely something really stupid, and you would have noticed it in a split second if you weren't so sleepy/tired/grumpy.
Turns out in the archives tab of Mod Organizer, I had all the BSAs under /data unchecked. I checked them all, and Fallout NV fired right up *facepalm*.
I'm not getting any indication that enboost is functional right now, so now I move onto troubleshooting that.
