Automated reverse engineering (of DRM) - https://news.ycombinator.com/item?id=7989490
Open-source debugger for Windows - https://news.ycombinator.com/item?id=8092273
It's an especially good way for teenagers to learn, before they get bogged down in the exam regime of the later years of high school, as they have insatiable curiosity and a seemingly infinite amount of time. In the hands of a curious teenager, a smart phone and an open-ended mandate to break it, could be a pocket sized, multi-year course in nearly every aspect of electronics and programming.
That being said, I don't think the $200 Chromebook is going to cut it. Eventually he's going to want to run a Windows VM.
As far as learning and reversing goes, it has often been helpful to see how something is working while also attempting to make it work for me.
Did you end up buying the Acer C720?
That will be the one I more than likely go with. I was worried about 2GB of RAM coming from a Windows background, 2GB isnt anything. But apparently it runs fine in Ubuntu.
it's still somewhat expensive though.
It also have a book - http://maijin.github.io/radare2book/
Not yet complete, but also evolving. Also you can read our blog http://radare.today/
And for the justice - there is another competitor - Hopper disasm too.