There are many different approaches you can take. If I were doing this I would definitely avoid having to parse a word document and just develop a GUI where all the information is entered into and then generate the documents you need. Depending upon your needs it might also be beneficial to store the data in a database if you ever need to update or regenerate those documents at a later time.
If you go the other route the word document that you parse must strictly adhere to a template otherwise any changes in formatting of that document could break your parser. Im in that situation now with a parser we have written in Python that parses Excel spreadsheets. If you go with Python there are 2 libraries to choose from for working with MS files. The one I use is called win32com which just gives you complete access to all the COM objects and the other one is called PyWin which is not very well supported and is a custom interface to working with the COM objects so you don't always have access to all the COM objects, just what they support. It's been many years since I've used Java so don't know what libraries might be available for working with MS files.
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