Who will be filling in this form? People in your own organization with access to the documents on your server or shared folder?
How large are these documents? Are they just plain text or are they documents with formatting and maybe graphics? How many of them are there?
Do you have a Word doc that inserts files based on checkboxes to look at? If not, why checkboxes?... Are you thinking you can insert multiple files if multiple boxes are checked?
Do you have any experience as a programmer?