You're probably correct in your first point, I should introspect on why my first instinct was to manage their experience myself. I am concerned that a randomly selected article might put them off for the reasons I mentioned above.
Your second suggestion is likely to be extremely effective from the sounds of it. I wouldn't worry about the dark arts elements, if we are finding areas they are interested in already, and they are already rationalist-ish they will likely agree with the main points anyway, and be impressed by the overall structure.
I've recently been trying to introduce some of my friends to less wrong. As a starting point I've linked them to HP:MOR and 'Three worlds collide' on the basis that they are both entertaining and accessible. But I'm not sure where to go next. Sending them to a main index page would likely be overwhelming, so could you suggest some sample articles to give them a general flavour of less wrong and envourage them to read more?
Qualities for such articles would probably include being:
What would you suggest?
[As I'm still a relative novice myself, apologies if a similar discussion has been had in the past and I haven't stumbled across it.]