MDODDIO73 - thanks for the response!
So, I would...
1) Check Condition - IF Contract Status = Active then:
a) Wait condition --> Process - timeout = 3 months BEFORE Contract End Date
b) Start Child Workflow ?
2) Check Condition - IF Contract status = Expired then:
a) Wait condition --> Process - timeout = 1 month After Contract End Date
b) Start Child Workflow ?
As for the Wait Condition, I am using the Form Assistant Dynamic Values. Below is what I have been using. Is this how you would set it up?