Connect check-out cleaning tasks with the next reservation

I assign my cleaners rotating cleaning tasks to keep up on deep clean and seasonal items like moving furniture, dusting, inventory, etc. I would like to create a rotating task that I can have repeat on a specific basis that I choose that will send a notification to the cleaner via text or email but it should be tied to a check-in/check-out date. Example, we clean blinds every 3 months and we deep clean the oven every 6 months. I would like to have a notification option like a checklist sent to the cleaner with the task every 3 months for the blinds and every 6 months for the oven but the notification should be send on the day of a turn so it is actually done and not forgotten about.