I appreciate your frank and honest answer; however, I am apt to disagree. I can go buy web hosting from myriad sources and secure a contract beyond one year (even from sources where CMS is integrated into the hosting, e.g. Media Temple's Virb). Any of these places could go bankrupt and then I am left to transfer my site, etc., alone. Despite WP's changes, I'm far more concerned with the 'what-ifs' than them having to deal with an automatic update.
I do run sites for other groups (and my own personal one) and here are my main concerns with .org:
1) Web hosting and security: Using .org means it is my web host and my responsibility to ensure the site remains secure. Given our limited funds (again, we're non-profit and all members are volunteers), it is unlikely to have the ability to purchase hosting in which all security measures are automatically updated. What happens if a crucial update comes out whilst the web master is unavailable?
2) 'Breaking' the site: if the webmaster updates the site in whatever way and manages to bring it down, the web master will have to have the coding expertise to fix it. Moreover, a poorly done update may force the web host to shut down the site until the situation is fixed.
3) Hacking: If the site were to be hacked, a web host may not provide the support to get it back up and running.
4) CPU usage: If the site gets bombarded (with spiders or people), web hosts may shut down the site. Again, if the web master is unavailable--what would happen?
I believe a CMS with integrated web hosting is our best bet. The less updating the team has to do in regards to SECURITY, the better. We are currently using the Blogger platform, which is simple and intuitive, but far too limiting for our future needs.
But of course, my current concern is our possible future funding, which would be in a lump sum, and I'd prefer buying multiple years if possible.