Bootable USB drive to open PDF or HTML file

We have a requirement to produce a USB drive which when inserted automatically opens up a PDF/HTML file. The PDF/HTML file will have additional PDF files the user will download. We can code the PDF/HTML to do that. The client wants to have control to update the additional files whenever they want. First part of this project is to propose the solution to the client by showing them a basic working model. So you will first prepare a working model for us to do the above. The second part of this project will be put under a separate bid request and may contain additional requirements from the client. The second part of the project will be given to whoever is successful in this bid. We are open to suggestions on the best way to do this so please explain clearly what you propose and what technology you will use.