I read your post out of an interest in reading about my most prominent diagnosis from childhood and was a little appalled, though happily, to find out that you know about much of what you are talking about. However, there was one small thing that irked me. Where you say "He will typically wear old, ratty clothes to school. This is not necessarily because he has no interest in fitting in, though. He simply finds old clothes comfortable and familiar. " and where you say "Subjects like math and programming seem to be the easiest, since the concepts are more structured and follow certain rules." These do not seem to be consistent 'symptoms' of Asperger's Syndrome. My behaviors as a child and now, for the most part, match everything else you have described, though.
But back to those quotes. I never cared to dress like all the other kids. I cared more about making myself happy and comfortable. The only thing I cared about other than the designs on my clothes was that they were clean and somewhat new. Also, until this past year in college, math was my weakest subject. However, as an example, I still prove your point about Aspies doing best at subjects that have rules. English has tons of rules that I can't remember the names of and it was and still is my absolute best subject (other than drawing cartoons, but that's another story). I learned the rules starting at a very young age and since then, when I would write, I would remember all of the rules subconsciously and obey them all.
Also, you might want to mention the idea that a lot of Aspies seem to be extra sensitive to lighting and noise. An Aspie like myself could get picked on in school for freaking out in reaction to the way a room is lit or for spasing when the fire alarm goes off. And in response to the person above me, there may be a level of Asperger's Syndrome where someone may not be able to feel empathy, but if you work with the person for long enough, they will get better. To an extent, though, I am not quite sure I understand, because I grew up feeling all the emotions on the inside. But if someone had told me they were tired and I was sitting in the only available seat, as a child or younger teen, I would have thought to myself, "Well, I could move over and let her sit down, but what if she is just joking? If she is, if I move, she's just going to laugh at me and that'll be one less friend I can have." You see, it isn't that we don't feel empathy, it is that we get generally confused or lost, trying to decipher what the other person actually means.
And this brings me to another part of this subject. A lot of Aspies seem to have trouble reading facial expressions or voice tones and, in turn, have issues reproducing those same actions in conversations with other people. My mother had to work with me for more than ten years before I finally learned how to change my voice as if I were reading a good book out loud and to know when to smile, when to lift an eyebrow, when to change subject in a conversation. It took her ten years of hard work with me and I'm still not perfect. I'm not like other people. I don't remember to do these things subconsciously. In fact, as I am talking, I have to actually remember every little thing she taught me, which sometimes makes it harder to focus on the conversation at hand without making an awkward silence.
Since I have been "trained" to get embarrassed when I "mess up" in conversation, I often wind up clamming up and forgetting to smile, even. It isn't that I don't like the person I'm talking to, it's just me being afraid to mess up after all the times my mother has scolded me for messing up. But on the occasions where I decide to ignore my will to clam up, I get things done and feel like I could be a leader if I tried. After all, I'm not so bad at giving speeches. I suppose if I wrote a speech for a campaign and read it loudly and authoritatively, people would listen.
Well, I'm sure all that I wrote sounds like a confusing mess, but in short, I was diagnosed with Asperger's Syndrome in the third grade and have come a long way since then, according to my friends and family. And here's a random fact about myself to back me up on my emotions thing. First, if you can't empathize, you can't sympathize. When I was little, when I would watch the Rankin & Bass Rudolph TV Special, upon finding out that no child wanted to play with any of the Misfit Toys, my heart sank and I wanted to grab them all up in my arms and have a party for them to cheer them up. And I still do, despite the fact that I am in college and I no longer play with normal toys on a daily basis (the only exceptions being my collectibles like my super rare InuYasha doll and the Astro Boy 2009 series 1 figure I got at Disney World. I sometimes play with them a little.).
One last thing. This came to mind when I mentioned two of my toys. After mom taught me better social behavior, it seems that my current obsession changes more frequently than it used to. Even though it was anime and manga for the past ten years (and each year a different series), in the past two or three years, it has been Walt Disney, Broadway Musicals, Tim Burton and Jim Henson -- all at the same time. Although, when I look back at my anime and manga (which I still love and enjoy), I always think, no matter how many animals I have liked in the past, I think my top favorites will always be InuYasha, Pokemon, Death Note and Astro Boy. I think that something that my mom did has caused me to have multiple obsessions simultaneously and sometimes I find it really weird.