Is there a way to create a year-level overview of a journal property?

I’m thinking about how to do homeschool planning and tracking for the upcoming school year. Last year I annotated a PDF of a year-view calendar to keep track of days that we did school and days that we got interrupted.

I can easily track this type of data in a property on the journal page for each day. Ease of entry would be improved over editing the PDF. But I’m not sure how I would go about reproducing a high-level view of the data.