I REALLY, immensely enjoyed the OP's thoughts on the challenges surroundings Aspergers blending in with the NT world. The "looking under the trees" thoughts particularly.
Well, I believe I've done my share of looking under the trees in the past, and you know what? I too am just as guilty of pretending and gaining with people who I found to be prominent for certain purposes; be it my university days, shared living situations, or office politics. I put up with a certain amount of negativity from a couple of people, who clearly wanted to use me for certain things, because they were socially savvy BUT I learned plenty from them as a result. Sometimes I had to pretend to be "with it", and I went to bars and clubs with this one guy and his friends and pretended to be normal (yet still exhibited some quirks) just so I could observe & imitate their behaviour as closely as possible even though I endured some mild-moderate ridicule and sarcasm. He clearly just wanted to use me to up his status b/c he looked socially superior with his high extroversion and glib superficiality and I was just part of the entourage. Also, this guy gave me lifts to places so I wouldn't have to take the bus, and let me use his CD collection. I let him use my computer in return. Because I exposed myself to that, I found that my social interactions improved later (you could say it was just the company I kept, but I'd disagree on that being the sole variable).
Also in the workplace in more recent years, I did engage in office politics but just not according to the same conventions as others. I didn't intuitively see the tribal nature of it all. In my dept, people hung out with each other & engaged in camaraderie and so forth, which for me was minimal, but I was very good at going the extra mile for people in other depts who were our "internal customers". I even got chummy with a couple of them b/c of their knowledge and the prospect that they could get me a better post in their dept. I would compliment this one guy on his insights and tact in explaining a certain technology. (Think Dale Carnegie's How to Win Friends & Influence People). Obviously, I was looking for gain. The unspoken rule though, was not to be too fraternal, giving or assisting to outside depts, so not having seen this part of the "forest", I found myself given the cold shoulder by folks in my immediate dept. It was a lesson learned. Even now I don't have quite polished instincts but I find it's a gradual process of trial and error with slow improvement. I think that we can approximate fitting in but never 100%.