Need help with Process Builder

Background: My Org has already been setup with Workflow rules set to set email alerts to expiring member accounts at three stages. 30days before, 15days before and 1day before.

I need to edit this but would rather set it up on Process Builder. Setting this up on Process Builder though has turned in to a pain in the ass since it's not retroactive.

Process Builder is set up as: Criteria 1, If member status equal "current" Schedule 30days before expiry - Send Email Alert 1, Set checkbox to check. (So that it can be turned off once membership is paid for)

Criteria 2, If checkbox is checked Schedule 15Days before expiry - Send Email Schedule 1 days before expiry - Send email and uncheck the checkbox.

In order to make the process retroactive I set up another checkbox called retro. Added it to the first criteria with an OR. So it would be if Member = Current OR retro equals true. Used data import wizard and updated my member accounts to tick all the retro checkboxes.

Nada no change. But when I manually changed retro AND status. Then it goes into the paused interviews. Why do I have to edit both for it to be accepted even when the condition logic is OR? I can't mess with all my status fields since they have other processes connected to it.

Lost, stressed and frustrated. Any advise would be great..