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send and stop email notification based on the requirement

Hello All ,
I'm attempting  a requirement  ,an email notification to be sent 100 days before the contract end date to the owner.We have few condition and a field  as "SRR" which will be updated once the email is sent.
Condition 1:
1)Once 100 days email goes out to the owner,Then the field "RR" will be done
it can be 3 situation :
a)If "RR" = Yes , then 90 day email will not go to  owner and it will start 60 day notification to customer.
b)If "RR" = No, then all email will stop (90,60,30,15)
c)If "RR" =  ,don't reply then and its blank then as reminder 90 days email will go out to account owner.

Condition 2:
Once 90 days email go out again it will have 3 condition.
a)If  owner say Yes then 90 day email will not go to customer .
b)If they say No then all email will stop.
c)If they don't reply then also all email will stop.

How can i achieve this?Any example or suggestions very much appreciated.