This guy is smart enough to come up with the TTS idea and work out the details (what app to use, making sure it's safe, how to set it all up on her phone, etc.), but dumb enough to not go to a pirate site and find a DRM-free version of the book that he could just copy/paste into the app? If it's old enough that she grew up reading it, it's definitely there.
It would've been better to have him set up the app and text in one day, and then have him spend a couple days helping her learn how to use the app to communicate. They could talk and she could learn how to use the app while she learned more about him.