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LessWrong comments on A Rationalist Guide to OkCupid - Less Wrong Discussion
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As for reasons, I can only offer some speculation since I'm 0/2 on being hot and/or a woman. First of all, I also spend a non-negligible amount of time on my appearance and I like people who are into my humor/intellect/interests/personality and not my looks. Commenting on appearance can also seem vulgar or indicate that you're only looking for sex. Finally, good looking women get complimented on their looks a lot, and not very beautiful women may be insecure about their appearance and question the sincerity of your compliments. I think this applies not just on OkCupid but in most online and offline situations.
Again, just speculating.
There's a difference: on OKC you can filter people based on whatever, in non-OKC situations you don't have that information available to you. I only have the woman's looks (and the women have a perv-o-meter) to notice.
Re-reading your article I think a better way to describe this is "approaches with comparative advantages" and "approaches without comparative advantages".
You have context. If you meet a woman at a bar, she's probably the kind of person that hangs out at bars. At an Iron Maiden concert, she's probably a metalhead. At a climbing gym, she's probably athletic and at least a little outdoorsey. Even if you just ran into her in a Starbucks, it's still one Starbucks in one neighborhood, and she was there and not somewhere else for a reason. You're filtering, but you're filtering less on what she wrote in one of the little boxes and more on what you both bothered to show up for -- which can actually end up being a stronger filter.
And if you talk to her for a couple minutes, you have more than that. That's true on OKCupid, too, but striking up a conversation there is a stronger indicator of interest than it is in person, so people might be more reluctant to indulge it.
I think I referred as "comparative advantage" to something different from what you mean. I was speaking to the advantages of the person hitting on someone: all else being equal you should focus on fora where your skills come to play. If that forum is large enough (like OkCupid), I think it makes sense to focus on that exclusively. In any situation where you meet potential dates specific skills matter and some people are better than others.
For example, I'm at a strong comparative disadvantage when hitting on people on the subway because I have a really goofy accent that people don't expect from my appearance and it lconfuses them. Someone who looks hot and has a great voice will do well on the subway without needing any context or background info on the person they are talking to.