Create a printable document from template
This use-case is perfectly normal for Drupal, but you're better off not using Word at all.


Create a content type (let's call it fillable) that contains all of the fields you require including an Image field which requires the ImageField module.
Give your users the 'fillable: Create new content' and any of the other relevant permissions for that content type that you wish them to be able to do.
Edit the content type and go to the manage display tab, determine how you want the fields to show (with labels? as links?).  If you need to group fields you can use the Field collection module.
Use your theme to make the node page layout how you want it to be
Put a print.css file in your theme and use that to fine-tune how the document prints


If you want to make other changes to the output of the node (like extra text in certain places, or complicated formatting), you can create a node template for that specific content type by giving it a name such as node--fillable.tpl.php