This would likely be accomplished easiest in individual smart campaigns (one for logic one, one for logic two) using wait steps for both scenarios, rather than in an Engagement Program. Both scenarios could use clicks and opens triggers, then further utilize advanced flow constraints to ensure the correct email gets sent. The wait step flow can also ensure that the end time occurs Monday through Friday.
Thanks Mariah! I had originally set it up using smart campaigns, I guess I need to revisit that. thanks for the advice.