This is a great summary with lots of specific, actionable detail. I successfully transitioned the Boston meetup from "philosophy and science fiction ideas discussion group" to "awesome vibrant community," so I'll give some feedback.
The most important thing in making the transition is to have content at the meetings, such as presentations or focused discussion topics. It sounds like you're doing this already, and having some trouble with the execution. Some suggestions:
—Relying on people to prepare ahead of time doesn't work in practice, since not everyone will actually do the homework.
—Having someone prepare a talk is a great way to provide background info and a focus for later discussion. I bet a 10-minute, well-rehearsed presentation on mind-killing would've improved this meetup dramatically. Doing this reliably does take a bunch of work, so it's good to have several people willing to share the responsibility.
—It's really good if you can set up the space in a way that encourages people to break out into individual conversations. My best experiences at meetups have been in conversations with 3-5 people. It's also helpful if you explicitly establish the social norm that it's appropriate to leave a discussion when you're not engaged, both because listeners don't have to politely sit through stuff they don't like, and because speakers can trust that people actually want to hear what they're saying.
I'm happy to answer any questions or help brainstorm for future meetups. If you want to talk more, PM me to set up a Skype call or something.
Thanks a lot for the input, Ben. The meetup has people trying to be heroes; we just need more practice. I'll install those social norms. I'll PM you if I have any more questions.
If you had an interesting Less Wrong meetup recently, but don't have the time to write up a big report to post to Discussion, feel free to write a comment here. Even if it's just a couple lines about what you did and how people felt about it, it might encourage some people to attend meetups or start meetups in their area.
If you have the time, you can also describe what types of exercises you did, what worked and what didn't. This could help inspire meetups to try new things and improve themselves in various ways.
If you're inspired by what's posted below and want to organize a meetup, check out this page for some resources to get started! You can also check FrankAdamek's weekly post on meetups for the week.
Tell us about your meetup!