There are two options for handling dates in an automation - either having a number and incrementing it each time, or setting it to the date it was last run. The latter option allows for easily identifying old and new dates without the need to reset numbers. Another option is to use something less frequently, which could be a good idea in certain situations. When deciding on the structure of the automation, it can be beneficial to have it as its own tier or at the first level, depending on the specific requirements. The choice between using reminders or a pre-filled task item can be influenced by future updates and changes. Overall, there are different ways to handle date-related challenges in automations, and it's important to find the best approach for solving the specific problem at hand.