In answer to your post Kimberly

Our staff will fill in the form ,all documents including inserts will be on the server.

The check box was my idea for completing the form
In simple terms the master document is a word file containing a table the files to be inserted are plain text paragraphs no more than 500 words

An Example would be

Towing a Trailer [ ] ( select trailer)

This would insert a file in table column 2 named "trailer.doc"

Inserted paragraph would read....

" When using a trailer it is important that the weight of the load is known and the load is secure and will not move during transport..............

My only experience of programming is machine logic programs.