It took me much longer than it should have to mentally move you from the "troll" category to the "contrarian" one.
I still find it tricky to distinguish if timtyler realizes what he's saying is going to be misinterpreted but just doesn't care (e.g. doesn't want to cave into the general resource-intensive norm of rephrasing things so as not to set off politics detectors), or if he doesn't realize what he's saying is going to be misinterpreted. E.g. he makes a lot of descriptive claims that look suspiciously like political claims and thus gets downvoted even when upon being queried he says they were intended purely as descriptive claims. I've started to think he generally just doesn't notice when he's making claims that could easily be interpreted as unnecessarily political.
Politics? This might, perhaps, be to do with the whole plan of unilaterally taking over the world? If so, that is a plan with a few politicical implications, and maybe it's hard to discuss it while avoiding seeming political.
I'm worried that LW doesn't have enough good contrarians and skeptics, people who disagree with us or like to find fault in every idea they see, but do so in a way that is often right and can change our minds when they are. I fear that when contrarians/skeptics join us but aren't "good enough", we tend to drive them away instead of improving them.
For example, I know a couple of people who occasionally had interesting ideas that were contrary to the local LW consensus, but were (or appeared to be) too confident in their ideas, both good and bad. Both people ended up being repeatedly downvoted and left our community a few months after they arrived. This must have happened more often than I have noticed (partly evidenced by the large number of comments/posts now marked as written by [deleted], sometimes with whole threads written entirely by deleted accounts). I feel that this is a waste that we should try to prevent (or at least think about how we might). So here are some ideas: