It's not difficult at all. The person who's organizing it simply chooses a restaurant that will be able to accomodate the group, and makes a reservation. People will come if:

(1) The restaurant is mainstream enough that the cuisine choice doesn't turn a lot of people off, not so expensive that it is unaffordable for most people, and located centrally enough so that it's not a long trip to get there.

(2) People have been given enough advance notice (a month is best) to be able to plan for it, and it's on a night when a lot of people can make it (i.e., a weekend is best).

(3) There haven't been so many other FlyerTalk events recently that people feel saturated.

The difficulties come in when no one has stepped in to organize (I think this was the case last week, when EPS ended up being the de facto organizer but very late in the game), also when there is not enough advance notice (I didn't hear about the even until a coule of days before it happened, when ChanelCinq e-mailed me). In addition, we have been having a lot of events here in SF of late (i.e., squeakr's dinner in honor of mjm, dinner with spiff) so enthusiasm might be a little down.

So many FlyerTalkers from out of town come in and out of San Francisco that it is difficult to entertain everyone! That does not mean we are standoffish here or difficult - actually, it's a really nice group. But it can be difficult to get groups together on the spur of the moment!