Thank you for the answers here, azircon. That question was very important and your answer was just as insightful.
Retention is probably by far the hardest to do as it's always a day in - day out kind of thing in the community. Keeping the community engaged is the most important thing and I think a constant reminder of why the community exists and what the goals are should always be reinforced so that the members don't lose sight of the goal.
For entitlement, I think it goes both ways. There is also potential entitlement for newer members especially if they don't know any better and it's up to us as a community to make sure to remind them that nothing is guaranteed and that you also have to build yourself and your reputation.