If you have already decided to spend many tens of hours reading, then perhaps doing the sequences in order would best achieve that. However, if you have already so decided, you probably need to read this first and take it heart.

If you have decided to spend a few tens of hours, there are 62 posts on commonsenseatheism.com in an ongoing series called "reading Yudkowsky" that outlines chunks of posts, also in order.

This article is a good one to start with, and you can see how the wiki here summarizes concepts from such articles.

Asking questions is always perfectly fine.

A web search for videos and podcasts by Yudkowsky are potentially very useful for certain types of learners, as they contain visuals and the cues of communication that are lost in the text format.

I recommend thinking about some things you are looking for from a post in terms of style and what you want out of it, asking many people what they think would be best to start with based on that, seeing which responses were common, and working to understand those, if it takes effort. Then, I would describe briefly in a discussion section post which of the commonly recommended posts you liked and why, as well as which of them you disliked and why, and ask for further recommendations based on that.

I think this is a good approach to the material because one asks for optimal posts based on one's own criteria. There are advantages to the sequential way, as the posts were written to be read that way.

Here is one person's top fifteen list, of which (now these have been recommended by two people) I recommend this this and this.

It may be that other writers happen write more in consonance with how you think, in which case you might want to look at Yvain's posts, of which this, this and this are some of my favorites.

It may be best to start by reading the material easiest to digest, which may be in story format - similarly, dialogues are often relatively very accessible.

You've given me some information, so my advice for which particular ones to read wouldn't strictly be my favorite posts. I think the first two I linked to from lukeprog's favorites help show that some ideas that are deeply theoretical are also totally natural.

Here are some links to some posts I think would make a good introduction.

If there is only one piece of advice that is more important than any other, it is the following: DON'T PANIC.

Welcome to LessWrong! The sequences are the most systemic way to approach Eliezer's postings; if you have specific questions, you can raise them here or in the discussion section.