I always, always check my email campaigns about 7 days after launch to ensure there are no issues with email send. The most common issues I've encountered are 1) no emails sending 2) emails sending daily, over and over again, to the same people.
In the case of this expiring membership email (v2) no emails were sending. Can you spot the difference between v2 and v3, the difference between an always 0 audience and the actual target audience?
Based on this example, I believe that "Greater than" is *actually* "Greater than or equal to" which is why no one was pulling into the audience. Very helpful distinction since we are trying to email people right at 90days.