I've had my frustrations in upgrading some sites -- mainly the first couple I built (initially in 4.5.0) where I made many mistakes. But I've always tried to take it all in the spirit of the Essential Given of Drupal: no backwards compatibility. I always covet the new features, so I tend not to linger long on previous releases ... but I do have clients who are not so up on the Drupal worldview.
So.... I added a page under "Is Drupal right for you?" when I did not find something similar. (If I missed something obvious, please let me know.)
Your corrections, improvements, lacerating critiques are invited and welcome. I'm just trying to get a start going here on helping new folks understand the essential philosophy that enables Drupal to be as great as it is.
I'm hoping that this may lead to some "best practices" for easing upgrades in the future (such has trying to avoid depending upon cul-de-sac modules that lose support, or not hacking core modules for short-term convenience).
What do you all think?
Laura
pingVision, LLC
4450 Arapahoe Ave, Suite 100
Boulder, CO 80303
303.415.2559