Instead of having Insider columns on the site, why not make it an exclusive feature in a weekly-monthly newsletter?
The "Insider" could possibly handle the content of this newsletter, and will craft agreements with the writers as he/she will be a reporter, who will gain access to inside scoops, and so on.
I just have a feeling, that between the very long updates, we lose a lot of people who would otherwise visit with regularity.
Anything we can do to keep people informed, and involved, are welcome ideas.