I'm not completely sure I understand what you want to do.
Unfortunately, you cannot use date operators such as Month() in an aggregated measure expression.
We do have Periodic operators in aggregated expressions, which can make calculations such as the year-to-date monthly sum. I'm not sure if that would be helpful to you with your date ranges however. Possibly some combination of filters on the date ranges (or on your "Categories" variable) plus a year-to-date periodic operator (CumulativePeriod) might help.
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