I think the greatest issue with Less Wrong is that it lacks direction. There doesn't appear to be anyone driving it forward or helping the community achieve its goals. At the start this role was taken by Eliezer, but he barely seems active these days. The expectation seems to be that things will happen spontaneously, on their own. And that has worked for a few things (is. SubReddit, study hall, ect.), but on the while the community is much less effective than it could be.
I want to give an example of how things could work. Let's imagine Less Wrong had some kind of executive (as opposed to moderators who just keep everything in order). At the start of the year, they could create a thread asking about what goals they thought were important for Less Wrong - ie. Increasing the content in main, producing more content for a general audience, increasing female participation rate.
They would then have a Skype meeting to discuss the feedback and to debate which ones that wanted to primarily focus on. Suppose for example they decided they wanted to increase the content in main. They might solicit community feedback on what kinds of articles they'd like to see more of. They might contact people who wrote discussion posts that were main quality and suggest they submit some content there instead. They could come up with ideas of new kinds of contentLW might find useful (ie. Project management) and seed the site with content on that area to do that people understand that kind of content is desired.
These roles would take significant work, but I imagine people would be motivated to do this by altruism or status. By discussing ideas in person (instead of just over the internet), they there would be more of an opportunity to build a consensus and they would be able to make more progress towards addressing these issues.
If a group said that they thought A was an important issue and the solution was X, most members would pay more attention than if a random individual said it. No-one would have to listen to anything they say, but I imagine that many would choose to. Furthermore if the exec were all actively involved in the projects, I imagine they'd be able to complete some smaller ones themselves, or at least provide the initial push to get it going.