Back again to answer my own post after messing around some more. Combining all of my redundant shots together seemed to allow TBC to see the loop. I guess the fix from here on out will likely be just combining points in the office, not sure why the field shot on my first setup as a check shot wasn't viable for the loop. Also not sure why it interpreted my first backsight of the loop as a mean angle, but if it works, it works.