I think the larger question of rationality is, When is it good for us, and when is it bad for us?
I suffer more from too much rationality than too little. I have a hard time making decisions. I spend too much time thinking about things that other people handle competently without much thought. Rationality to the degree you desire may not be an evolutionary stable strategy - your rationality may provide a net benefit to society, and a net cost to you.
On the level of society, we don't know whether a society of rational personal utility maximizers could out-compete a society of members biased in ways that privileged the society over the individual. Defining "rational" as "rational personal utility" is a more radical step than most people realize.
On the even higher level of FAI, we run into the question of whether rationality is a good thing for God to have. Rationality only makes sense if you have values to maximize. If God had many values, it would probably makes the universe a more-homogenous and less-interesting place.
It's possible that one can learn the wrong kind of rationality first, but I disagree with the idea that rationality can be a bad thing in general.
The first skill ought to be efficient usage of computational resources. For humans, that means calories (no longer a factor outside our ancestral environment) and time. LessWrong has taught me exceptional methods of distinguishing my exact preferences and mapping out every contour of my own utility function. Thus, I can decide exactly which flavor Ice Cream will give me more utilons. This is neat, but useless...
I've been on Less Wrong since its inception, around March 2009. I've read a lot and contributed a lot, and so now I'm more familiar with our jargon, I know of a few more scientific studies, and I might know a couple of useful tricks. Despite all my reading, however, I feel like I'm a far cry from learning rationality. I'm still a wannabe, not an amateur. Less Wrong has tons of information, but I feel like I haven't yet learned the answers to the basic questions of rationality.
I, personally, am a fan of the top-down approach to learning things. Whereas Less Wrong contains tons of useful facts that could, potentially, be put together to answer life's important questions, I really would find it easier if we started with the important questions, and then broke those down into smaller pieces that can be answered more easily.
And so, that's precisely what I'm going to do. Here are, as far as I can tell, the basic questions of rationality—the questions we're actually trying to answer here—along with what answers I've found:
Q: Given a question, how should we go about answering it? A: By gathering evidence effectively, and correctly applying reason and intuition.