newspaper need help

I work for a newspaper publisher that produces 9 weekly newspapers. I'm looking into using Drupal as a CMS for our web products. I read Building powerful and robust websites with Drupal 6 which helped me to understand how drupal works and to set up a site. I really like how the New York Observer is laid out and could use some help on setting up a newspaper site.

Below is a list of what I'd like to do and would really appreciate any pointers or suggestion you may have.