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You will not be able to use a engagement program because you use different wait period between each content. I understand variable waits in engagement programs is part of the roadmap, but I do not have any ETA.
So that leaves you no much choices but use regular smart campaigns. Instead of running multiple triggers and etc... since you want to be able to catch up, I would create 1 distinct batch smart campaign for each of your email content and some smart lists that would detect the conditions to add people to each of these batches.
Thanks Greg. I appreciate the information and I'll take that approach.