I find myself in the position of being the head of a non-profit group started by a bunch of people with no planning skills to speak of, and no technical knowledge. I'm certainly not the world's best when it comes to this stuff, but I know my limits, I know people I can ask for help, and I'm not afraid to jump in and find a solution to problems when I see them.
My current beef is that rather than having someone in the group set up internal mailing lists using our domain name, they set up all their lists as yahoo groups - and there are now over 100 of these lists to manage. Besides the fact that yahoo irritates me, I think it'd be more professional to find an in-house solution.
Our current site uses metadot, but there are access issues, and it doesn't handle the yahoo group problem.
Drupal was recommended to me by several of my more technically minded friends, and I really like what I've seen so far. It looks like the Organic Groups modules would handle the same sorts of things we're using our yahoo groups for. The multi-site option of using the same membership database would be very helpful to me as well, as we have different content available to different membership groups within our organization, and being able to use subdomains for that would be quite nifty.
The one thing I haven't seen yet (and maybe I'm just not searching in a good spot) is a suggestion on how to migrate yahoo groups to a site using Drupal's OG modules. Obviously I can import content in one way or another from the list archives. I can get someone here who's a little better with mySQL to move our existing metadot users to Drupal without killing passwords and such. And I can pull an entire mailing list from each yahoo group...but just adding their email addresses doesn't give them access to the site.