How to Automate Testing a Complicated Microsoft Word Documents

I have a large number of complicated standardized legal documents in Word that need to be tested. The fields include a number of options that list out the benefits of individual health plans that are offered by our company. The government requires this document and has provided a table driven template for this document (Summary of Benefit Coverage). The logic to populate these tables is very complex and spread across a number of excel driven logic tables for testing (the code itself is in .Net). While we can do unit testing in .Net, we need to test that the documents actually printed with the correct information. The process to do this manually has takes us weeks to perform. What is the best way to automate the testing of this complicated logic?