FWIW, I did want to address the hole size discrepancy pointed out in the abbreviated excerpt below:
While it may not be a best-practice solution, under-sizing the holes was an intentional decision while still in 'measurement mode.' I originally began by looking at the holes' exterior profiles as the basis for determining alignment; see first pics posted where basing it off of angles alone. After finding that the photo quality made it rather subjective to judge where they end, however, I chose to move towards a more center-point-based measurement solution. As such, I created a quasi point-cloud based upon the perceived edge for each hole to find the center - and then measured out a 2mm hole from that so that I could still see all photo edges while still aligning the two. In retrospect, I should've explicitly stated all of that and so apologize for the confusion.