In your date token calculator, I believe you want to subtract 2 months from contract end date to get a date 2 months prior to contract end date.

In the Search Repository activity, it looks like you are searching for documents where the contract end date is between 1/1/1900 and Today which is the %(Date) token.  So if your contract end date is November, it's not going to be found.  You might even be able to eliminate that condition in the search and create another date token from the calculator and search where your contract end date is greater than Expiration Date - 2 Months and less than (Expiration Date - 2 Months) + 1 Week for example.