Notifications with Status and Date Columns

I have a scenario where we have Subcontractors that are schedule to do work for us. I would like an automation that will notify me if we try to double book a subcontractor. The bookings are created by an automation in another board.

My setup is I have a status column with the subcontractors names, then we have a timeline column that shows the dates they are reserved for. I would like an automation that will look down the status column, and take all matching names and then look at the Timeline column to see if any dates match or overlap. I would then like a notificaition warning me of this.

I don’t know if this would involve using some formula’s and maybe General Caster to send the result to another column? Or maybe this type of automation is not even possible? Any input would be appreciated.