I'm a member of a local astronomy organization. One of the ideas we had would be online observing challenges for the group throughout the year. Something like an individual ongoing Messier Marathon throughout the year as weather allows. We could then track the leaders and celebrate winners at our meetings. It would be a great way for our distributed group to connect online between meetings.
I like Live Sky because I use Sky Safari to track my observations. Ideally we'd be able to create separate challenges and have leader boards for the group. Do you have something online like that where we could create a group and non-Sky Safari users could log on and record their observations?
Come to think about it, the Astronomical League could use something like this to help with their observing challenges as well.