For the last few months I've taken up the habit of explicitly predicting how much karma I'll get for each of my contributions on LW. I picked up the habit of doing so for Main posts back in the Visiting Fellows program, but I've found that doing it for comments is way more informative.
It forces you to build decent models of your audience and their social psychology, the game theoretic details of each particular situation, how information cascades should be expected to work, your overall memetic environment, etc. It also forces you to be reflective and to expand on your gut feeling of "people will upvote this a lot" or "people will downvote this a little bit"; it forces you to think through more specifically why you expect that, and how your contributions should be expected to shape the minds of your audience on average.
It also makes it easier to notice confusion. When one of my comments gets downvoted to -6 when I expected -3 then I know some part of my model is wrong; or, as is often the case, it will get voted back up to -3 within a few hours.
Having powerful intuitive models of social psychology is important for navigating disagreement. It helps you realize when people are agreeing or disagreeing for reasons they don't want to state explicitly, why they would find certain lines of argument more or less compelling, why they would feel justified in supporting or criticizing certain social norms, what underlying tensions they feel that cause them to respond in a certain way, etc, which is important for getting the maximum amount of evidence from your interactions. All the information in the world won't help you if you can't interpret it correctly.
Doing it well also makes you look cool. When I write from a social psychological perspective I get significantly more karma. And I can help people express things that they don't find easy to explicitly express, which is infinitely more important than karma. When you're taking into account not only people's words but the generators of people's words you get an automatic reflectivity bonus. Obviously, looking at their actual words is a prerequisite and is also an extremely important habit of sane communication.
Most importantly, gaining explicit knowledge of everyday social psychology is like explicitly understanding a huge portion of the world that you already knew. This is often a really fun experience.
There are a lot of subskills necessary to do this right, but maybe doing it wrong is also informative, if you keep trying.
Why do you make a comment if you expect it to have net negative downvotes? I've always felt that I strongly agreed with how the community voted things. If it has three downvotes, it's probably not worth seeing.
Do you think that Less Wrong is really that bad at voting that some things need to be said which we'll downvote anyway?
I would have thought that "will be downvoted" is fairly close to "should not post."
It is certainly close to 'best not to post'. There are some times where posting things that you know will be negatively received is worth doing anyway. But it doesn't work well if you try it too frequently. You end up with a reputation as a crockpot at best either in general or specific to one topic. 'Qualia' and 'quantum monadology' spring to mind as past examples. Will is risking getting his own reputation on the subject of theism.