The Kindle doesn't use WiFi. The older Kindle's use wireless via Sprint that is always on and available forever. He could also email PDFs of eBooks to the owner's Kindle address and it'll be converted and downloaded to the Kindle. It is possible to install eBooks via USB connection, though. He needs to convert the books to the MOBI format, and there are a number of good free programs like Calibre. They'll also need to associate the Kindle to an existing account, which will happen when he turns on the Kindle for the first time.