I ended up answering my own question. It turns out the table calculation filters were not working because the default table calculation was always using Table (Across) instead of a more advanced table calculation that could be done from the context menu while the pill was on an existing shelf.
In this way the filter was using a table calculation with different addressing and partitioning schemes than I intended. I found that if I click on the table calc while it's on the marks shelf and choose filter from there, the filter will work based on the more advanced table calculation I created rather than the default. I'm sure there's a simpler way to do this, but this is what worked for me.
Cory we love these sorts of posts! Not only did you ask a good question, and provide a packaged workbook, but you ended up answering the question before we could get to it.
And best of all? You came back and posted the answer, included a good explanation AND marked your question answered.
I nominate you for the Best Asked & Self-Answered Badge!
Cory, we really do appreciate you following up with a correct answer and explanation to your question. It helps all those who follow/search the forums.