To answer your question about how we created custom regions, we got most of them by asking TownNews to layout our boxy regions per the image I attached above when they were setting up our Flex site. We have since added a few more because we do have people here who are template certified. Like most things, you think you have enough regions on a page until you start filling them up. It would probably be really helpful if users could add regions to pages without needing template access.

We took a different approach using the boxy layout on our http://lancasteronline.com site. We dropped the right rail completely. We don't use one anywhere on the site. Instead we added more regions within the layout and put our ads more inline with the articles. That way when the site goes from desktop to mobile, there are more places for the content and the ads to slot in around each other. We still had to deal with creating a second set of leaderboard ad slots so the ad would be visible when the nav is reduced to hamburger menu. The biggest challenges we've had with using this layout has been keeping columns relatively balanced so the tops line up with each as much as possible and figuring out when to allow the blocks to have the full width of the page.

Do you have anyone on your staff who has template access? If not, I don't think there are any settings that you can change that will fix your date display issue right now.