> 1. Finding space to have events
Talk to a coffee shop owner. Promise them your group will (reliably) order drinks or snacks. In exchange, every month we get an area "cordoned off" just for us.
> 2. Ensuring that people who said “I’m going” actually end up going.
Aside from sending a general newsletter, I personally ping and catch up with individuals. This is a lot of work. It pays off when they evangelize your event on your behalf.
> 3. Bootstrapping groups such that when I stumble upon The Offline Club, I can signup for something relevant to me, happening a short time from now.
See #2
> 4. Keeping organizers willing to continue hosting events
That's tougher. However, if the event is specialized/niche/unique enough, the organizers will be conferred high social status by the community.
> 5. Keeping away organizers who see it as lead gen for their sales job
Mmm, could we define sales job? On the business front, the meetups are used to promote our (indie) conferences. The meetup groups don't mind when I ask them to buy a ticket. They can just say no and we're not pushy about it.