Regarding the methodology/steps to help the guy: I do understand your point now and agree with all what you said, except the last bit - I still believe it's better for him to have even that chance than nothing. Even though this experiment might not make him a programmer, he will have a "motivator" in front of him for some time, internet connection and a laptop. This could (and I hope it will) change something in him when the project is over, no matter the end result with JS.
I see outcomes from this project as far from linear; for example: he might use internet to learn about something else he tends to understand easily, discuss that with his "mentor" and possibly end up working in that sphere. He has more chances to do something with that guy, chromebook and JS books than with nothing.
Hope this makes sense.