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Your calculation looks accurate, but in the first screenshot, there is an error because ["up to this date" filter] and ["just this month" filter] fields are boolean and cannot be used in that manner. However, you are encountering a separate but similar error in screenshot #2. In that screenshot, there is an error because in IF statements, the first comparison must result in a boolean expression and the calculation there is an IF then has a string. If "up to this date" is not a valid expression.
I was able to avoid getting the error (using the same calculation) just by changing the ["up to this date" filter] and ["just this month" filter] to strings. Howver, after looking at how those are calculated, they will also likely need modification to achieve your desired results. You may want to add another IF statement into those fields like IF MONTH([Filter By Date]) >= MONTH([Document Date]) then "True" else "False".
Hope this helps!