I would recommend starting with the fiction, especially if you have trouble with non-fiction explanations. It's much easier to understand the theory once you've been exposed to the concrete examples.

I'm with Eliezer on this one, that the vast majority of philosophy is utter nonsense and trash. Objectivism seems to be a shining exception to that rule, however. I am an avid reader of Hofstadter, and I have also been reading up some on the foundations of mathematics which seems like it might be interesting, and Objectivism has turned me on to philosophy in general, so I am on the lookout for more good work. The amount of cross-over between Objectivist style "rationality" and LessWrong style "rationality" is especially awesome, and it's unfortunate that there's such a lack of cross-over in the communities.

I'm not sure what you mean by "unconditional endorsement", however. My primary purpose here was to recommend some reading for those who would like to know more, but yes I do endorse Objectivism in general, for what that's worth. Also, even if I thought the philosophy was wrong, as an avid reader of fiction, the novels really are awesome in their own right. So I am endorsing those, too.

If you want to start an Objectivism thread laying out the problems you and others have with the actual philosophy, I would be glad to join in there, I think that would be awesome :) If not, I will probably create one myself at some point.

Well, that's the stereotype.

And Ayn Rand isn't very popular around here.