VBA If/Then Error Help Needed

Hi. I'm needing to add a new column ("O") to a worksheet that adds text alerts when any dates from column "M" fall outside a defined date range (first day of current year to last day of current month). The script keeps stopping at the first "If" line, with a "Run-time error '1004': Application defined or object-defined error". A few hours of Googling possible VBA solutions hasn't helped, but maybe I'm looking too hard. It IS Friday after all...

Thanks for any help!

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You're welcome and thaks for the rep points.