Yes, but it's often a hassle. You risk being accused of trolling, overconfidence, &c., and it's difficult to claim that such accusations don't have some tinge of truth.
I suspect it's not overall a very good habit and that I bring it to LessWrong mostly because it happens to work well in my personal rationality practice. On LessWrong it's probably better to put in a little extra work to find a way to go meta—don't support a side, but show clear not-introspectively-obvious reasons why someone could hold a belief that was to them introspectively obvious and thus difficult to explain. I generally like the anti-democracy LW commenters because they seem to have practiced this skill.
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: