If you're looking for shortcuts, perhaps start with:
I am not sure how approachable the above will be to a "rookie", because I can only speak from my own experience. I read Drexler's Engines of Creation, and Kurzweil's The Singularity Is Near and was fascinated by these topics. I kept finding LessWrong on Google searches about them and I thought the writing was good (especially Three Worlds Collide). So after jumping around a bit as I discovered LessWrong in the first place, I read the original blog posts that went into R:AZ in pretty much the order written. I did end up downloading an ebook version of Eliezer's posts to do it (not the slightly reorganized R:AZ ebook, which was not available at the time), which I read on my phone in my spare time.
In my opinion, you should at least try to read all of the R:AZ sequences, even though there are more than 9. It's quite long, but you'll get insights from it long before you finish.
There's also some redundancy as the concepts build on each other. So if you're struggling getting through an essay, I would say read it aloud and move on even if you don't completely get it. (This might be easier with the audiobook.) Some essays are easier to read than others, and I think that some are more valuable than others.
If that's still too much for you, I can try to point out the individual essays I think are especially important:
- Raising the Sanity Waterline links to some critical earlier posts, which makes it a kind of mini-sequence. It's also got a key insight in its own right: humans are insane, and this is not OK.
- Beyond the Reach of God — Perhaps the most powerfully written essay in all of the Sequences. Nature is crushingly indifferent to human well-being. Everything is allowed to go horribly wrong. There are no guardrails until we build them ourselves.
- You Only Live Twice — There’s a big difference between mostly dead and all dead.