It would take more information to properly determine what the best starting poing would be for him; but if he has not used a web browser I suggests starting w/
1. email setup
2. google
3. facebook
etc... basically as much basic computer usage as possible; IMO rails classes like that and pretty much everyone else is going to assume their audience is comfortable w/ computers and other modern day technologies.
So this is one of things I was specifically looking for: Exactly what does he need to learn immediately? What is the best set of tools he should experience and submerge himself with to really understand the internet, both as a consumer and as a potential creator?
I'd be willing to pay the tuition if it's really useful for someone who has still not ever seen/used a web browser.