In general, it is difficult to make a TABLE do this. I suppose some tricky default value specification could do it, but the problem is that you are not supposed to have code in a table. You have code in a form or query or report. You can accomplish this by having a startup form that triggers a couple of queries to update required items, but this is the wrong mindset because it is still an impure situation. (What do I mean by impure? Keep reading.)
A table is supposed to be PURE DATA. What you are requesting this checkbox to be is an impure datum that depends on something outside the table. As such, it can NEVER be considered normalized. (It contains something that depends on an item other than the prime key.)
You might find a simple workaround here and there, but this is a VERY BAD mindset to stay in. You should NEVER look to a table to do a query's job. In a query that was based on this table, you can have an expression in one of the fields that compares your target date vs. today in an expression using the "<" or ">" operators. That yields a true/false or yes/no answer that ALWAYS shows the correct state.
Further, almost anything that you can do in a table can be done through a simple table-type query.
