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as you can see the header has plenty of space extra room above and below the word "January" but once i resize the table to remove the unneeded space it says my text is too large. Am I overlooking something? I create tables all the time and never ran into this issue
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InDesign tables are not, for the most part, auto-adjusting as they are in Word. You have to more or less manually scale everything to work as intended.
So you have to consider three factors in fitting text to table cells —
It's easy, in early stages, to have too much default/legacy spacing involved, which will limit how small you can make cell margins around text.
Set ALL spacing to zero for table text and cells — use styles for both! — and then selectively tweak it to, for example, vertically align text in header rows.