I really like the idea of creating bounties. Any kind of official way of creating a bounty would also serve as a focal point for people to offer more material rewards. I don't have a problem offering a cash reward for people donating their time for important tasks, and I suspect there are others like me too.
I've been browsing LessWrong less often as of late, and I believe that one of the reasons is because I don't want to get all excited all over a new insightful LW post, only to discover that it's a meetup in a city that I'm not even in.
And for newbies to the site in particular, they're not going to see all the awesomeness of this site if they simply look at the frontpage and think it's a community just for meetups.
I'm sure meetup discussions can go somewhere prominent. Maybe a separate section can be devoted to them.