You could do this with a series of shared filters. So:
1 - Shared filter = Clicked on any email sent by us in the last 6 months?
Yes - Receive email 1.
No - Push to Shared filter 2 then into dated wait step before the email:
2 - Shared filter = Opened any email sent by us in the last 6 months?
Yes - Receive email 2
No - Push to shared filter 3 dated wait step before the email:
and so on..
The dated wait step will allow you to stagger the sends.
After each email, add these contacts to a shared list. This will allow for easier reporting and future, in canvas, segmentation.
It would look something like this:
Good luck.