Spent 6 hours trying to fix a simple index layout that should have taken 20 minutes

I was setting up a monthly spread for April and decided to try a new index layout where I group things by category instead of by date. Sounded simple enough. But I kept running into the problem of what to do when something fits TWO categories. Like a doctor appointment - is that health or errands? I redrew the whole thing three times before I just gave up and went back to a straight date list. 6 hours of my Friday shot. Has anyone else fought with the index system way longer than it deserved?

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