I have a client that is constantly complaining about not being able to copy/paste documents with images from MS Word into a wysiwyg to create content on their website.
And this will fail. MS Word does not create valid HTML, the pages will appear broken to users of conformant browsers. Word also has some odd methods of anchoring images and flowing text that will not translate. In short, Word is a poor environment for authoring HTML.
Of course your clients probably won't accept that which brings us to option 2:
Since your client has opted for Word as their WYSIWYG editor there's very little point pasting that content into another WYSIWYG editor. Your optimal solution is to look into ways of automating HTML export from Word or OPen Office. This could be done using a combination of VBA and a server-side script to first convert the document to HTML (this will also write the images to disk) and then upload the combined content to the server.