I was 27 when I was meet director for my first OUSA championship event. I think that is the youngest meet director for a championship in recent memory. Now that I am 32 I feel that I am older than a lot of the young crowd we are trying to attract to events, and I would be happy to be the old guy on a board or race organizing crew.
Unfortunately I am still the youngest at nearly everything in in orienteering organization that I participate in. I hope that the organization can move past the expectation that retired people are required for our sport to not burn our our volunteers. That that is even being suggested should be a wake up call that we are asking too much of volunteers in the first place! I hope to see the organization and sport move to a model where much more of the daily organization work can be performed by paid professionals so that all ages can enjoy the sport without a feeling of obligation to volunteer lots of hours now, or in the future.
If the willingness is there from the organization to change, I believe the resources from the community can be found to make it happen. Without a clear executive vision for where to go though, I don't see anything changing.
(Said from the point of view of someone who has tried to provide professional services to O events, but can't pay the bills that way, so is now going to be timing the highest level New England ski races this winter at rates that are sustainable. Should orienteering ever need my services I am always there to step in and make things happen on the technical front when the desire and drive from the organization are shown)