I managed to solve the problem between submitting my question and it becoming approved. My solution in case anyone else runs into this problem is below.
The problem seemed to be that I had tried to run tesseract with my .traineddata files in a location other than /usr/local/share/tessdata and it was confusing tesseract. I ended up creating a new VM, installing tesseract, and then installing my .traineddata files directly to /usr/local/share/tessdata.
This new tutorial was very helpful and mentions this step that the previous tutorial left out.
My guess is that this happened because I set a environment variable to a new location tesseract ended up checking both locations, finding the .traineddata files in one of them and not the other, and then printing the failed to load and the successful outputs. I would advise not trying to deal with the TESSDATA_PREFIX variable at all and making sure to install those files directly to where tesseract expects them to be.