Yep - it can be a challenge
We’re lucky to have people from around Australia all in Sydney for a GovHack event next month, so a meetup there is something that has just emerged as an opportunity.
How this could work via meetup.com is to simply get events associated with existing open data meetups (I’ve contacted the San Francisco meetup group about this - they have around 1,000 members). Even if there isn’t a large number of active contributors in a region we’d be able to have speakers join via Hangout to share their work and promote the project. Local Python meetups are also a great place to seed a CKAN focused event.
I’m happy to speak on behalf of the CKAN Association via Hangout at any event at any time. I’m also happy to share the CKAN deck with the info I normally present at 101 sessions.