Report that looks at more two or more criteria but the criteria do not all have start dates

Hi. I'm trying to build a report that will tell me when we are close to sending bills for a district to the print shop. The criteria is looking at two rows with different names in the Primary Column; i.e. Request Information and Original Proof Signoff but I need different criteria for each when it comes to dates. For example, When Original Proof Signoff has been completed and when Request Information has been started but not completed. The "When" criteria on Reports seems to apply to all of the "What" criteria. Is there any way to apply specific Whens to the different Whats?

Thank you,

Lori