I found it.
'It' being the point at which, at least for me, the layout of Ayn Rand's Objectivism breaks down.
Objectivism is one of the philosophies that (until now) I knew was off - could just feel it - but that I couldn't find the flaw in the logic. It was all consistent, and the premises made sense, but the conclusion was just plain wrong. Around my house, this is known as the Austin Powers phenomenon - you know, "Yes... Yes... No! No!" I get the same thing with Plato.
But I found the flaw. So there, you crazy Alan Greenspan-boning Russian.
The philosophy basically lays out like this. (My summary from reading the summary in the back of the Centennial edition of Anthem.)
1. What's real is real, and our job is to perceive it. Creating your own reality by perception = wrong.
OK, though I'm not sure I completely agree, this doesn't set off any bells. Go on.
2. We are reasoning creatures, and the best way to deal with everything is through reason (since our job is to perceive stuff and figure out what to do with it). We must be free to use our reason as we see fit, and therefore guide our lives as we see fit.
3. Therefore, we make our own choices. We are the captains of our own souls, so to speak. Therefore, everything that happens to us is of our own making - there is no such thing as a victim of circumstance - and therefore there is no place for altruism or charity, because that just subsidizes people who chose to make bad choices.
Ding ding ding! We have a winner!
There's a part 4, but it has to do with art and I don't care because I found the break point. Here it is:
You get where you are by making choices. Those who have crap lives just made bad choices so fuck them.
How do you learn to make good choices? You are taught, either through life experience or through schooling of some kind.
How do you get this experience and education? By learning from mistakes; by, say, going to school.
But how do you get into the school?
There's always a gatekeeper, whether physically or in an abstract sense. People who are poor and have crap lives don't get to learn to make good choices because they can't get the education/experience they need. They're kept out, by lack of resources, prejudice, what have you. They can't, say, make good choices with money, because they don't have enough to pay for school to teach them how, and they don't have enough to survive making mistakes and losing it.
That's what a true liberal (in all senses of the word) social safety net, both economically and culturally, is for. It helps people bypass the gatekeepers so that they can learn how to make choices. It's like the large-scale version of not punishing a kid for mistakes made in the process of learning. You can see it in job training programs, public education and healthcare, and welfare (when done right): not punishing people for being born poor. You can see it in making abortion, adoption, birth control, emergency contraception, and sex ed widely available and accessible: not punishing people for having sex. Because shit happens in life, and the world isn't fair. And if Ayn hadn't been so scarred by the Bolshevik Revolution, I expect, as she's clearly clever, that she would have made the connection.
So there, Ayn. I win. You can't make my brain hurt any more.