Any way you do it, upgrading an organizational website to a new major version of Drupal - for example, from Drupal 5 or 6 to Drupal 7 - is a significant task.
Change can often be a hard thing for groups—even progressive groups. Getting a staff team to willingly adopt new software or a new website can be challenging. Especially for staff who always feel a shortage of time in getting the important work done.
In a recent blog post, Drupal 8 co-maintainer Alex Pott highlighted a seismic shift in Drupal that's mostly slipped under the radar. In Drupal 8, he wrote, "sites own their configuration, not modules".
As part of a long-term collaborative partnership with the University of Victoria's Geography Department, Chocolate Lily has been working on producing a customized version of Open Outreach suitable for community mapping.