Well, there's three kinds of meetups I can imagine.
(1) You go for the intellectual content of the meeting. This is what I was hoping for in Santa Barbara. For the reasons I mentioned above, I now think it's unlikely that the intellectual content will ever be worthwhile unless somebody does some serious planning/preparation.
(2) You go for the social enjoyment of the meeting. I confirmed my suspicion in SB that I personally wouldn't socially mesh with the LW crowd, although maybe this was a small sample size thing.
(3) You go to meet interesting people. In my life I've had a lot of short-term and a few long term friends with whom I've had fun. But I've probably only known 3-4 truly interesting people, in the sense that they challenged my thinking and were pleasing enough to spend a lot of time getting to know well.
Any of the above would get me to go to a meetup, although I'd be most excited about (3).
The NYC group, and olimay in particular, has certainly challenged my thinking. I might be coming from a very different place than you, however.
For those who don't yet know, there has been a thriving rationalist community in NYC since April 2009. We've been holding weekly meetups for the past several months now, and often have game nights, focused discussions, etc. For those of you who live in the area, and not yet involved, I highly encourage you to join the following two groups:
This Meetup group is our public face, which draws new members to the meetups.
This Google Group was our original method of coordination, and we still use it for private communication.
The reason I am posting this is because there has been interest by several members in sharing an apartment/loft, or even multiple apartments on a floor of a building if there are enough people. The core interest group is going to be meeting soon to figure out the logistics, so I wanted to extend this opportunity to any aspiring rationalists who either currently or would like to live in NYC. If you are interested, please join the Google Group and let us know, so that we can include you in the planning process. Additionally, if anyone has experience living with other rationalists, or more generally in a community setting, please feel free to share your knowledge with us so we can avoid any common pitfalls.