I think you're making it out to be more difficult than it really is. Many people learn to program having their first language JavaScript and their first platform be the browser. Based on my perception of Dialects' intelligence, I don't think document.write(text); document.write("<br/>"); will be a major bump on the road for him.

Besides, if he is really that averse to HTML, you can write console apps with node. There is no requirement that every script run with node be a client server application. And he'll still be practicing JavaScript.

I know what you mean ... but I think that you have a wrong impression because you learned about HTML and CSS incrementally over time.

For people who have been following HTML it might be trivial.

But after that quote ...:

I'm quite lost in terms of where I should start especially given the monstrous array of possibilities.

... I thought it made sense to point out that for developing with those high level techologies you should read up on the "what happened so fars ..." and break the research aspect of learning down even more.