@GlinetteC @ReyJohn_D @AileneA @KlentB @ReymondO 

I have now confirmed the answer I posted works for this issue.

The issue that needs to be solved in order to re-import a web connect file is to modify the transaction IDs inside of the QBO file so that for each successive import, they are unique. 

QBDT stores the transaction IDs of each import in order to protect the end user from duplicate data. If the end user WANTS duped data, the only way to solve is by making each transaction ID unique from the previous import.