This was a really helpful article. I'm a co-organizer of Oahu Online Entrepreneurs in Hawaii. While we have a broader scope towards Internet marketing, WordPress is a popular topic.

I can totally identify with the headaches of scheduling and organizing meetups. A couple of months ago, I went through the search for a new venue. Nearly impossible to achieve that ideal convergence of central location, free parking, good Wi-Fi, available seating, and coffee.

One problem is trying to keep a balance between pros and newbies. If there are too many pros, the newbies feel intimidated. If there are too many newbies, no one is able to learn from each other.

It's a labor of love for me, though. The most common compliment we get is, "It's so great to meet other people who are doing the same thing." Blogging, programming, etc. can be lonely professions if you're a solo freelancer based at home. The meetup is really valuable for meeting like-minded people and feeding off the collective energy of the group.

I've also picked up tons of insider tips and resources I could never have discovered on my own. I take detailed notes and write recap reports on our Meetup.com "Discussions" page, and those things can end up really long. I'm constantly blown away by how generous the members are in sharing what they know.