As we can see, there are not just one problems for the new comers of the community to work easily with dotlrn, I would suggest that if we the new users of dotlrn could come together to do the following:
1) On the Wiki area, we can set up a question and answer list so that easily solved problems can be highlighted and resolved. For example, as a FreeBSD user, I spent a lot hours figuring out how to install dotlrn/ACS using ports. Now, my notes would save hours for other dotlrn new users but would be rubbish for the experts.
2) For some commonly-seen problems for the new users, we can come up with some small funds (from individual users) to hire experts to come up with recipes of solving these problems. Many small funds together can be decent amount of $ to hire experts. These recipes should be put in the section of the new users so that the increasing new users can easily find them, and experts won't be bothered with the unfresh ideas.
The vitality of a healthy community depends on both experienced experts and new users: the formers lay solid foundations while the later let the community grow. I really believe this software is the greatest among those I've seen both in CMS area in general and in VLE in particular. Yet, to be really good at it needs a lot of time and belief.
As a new user, I wholeheartedly thank all those who have done, and have beening, wonderful job both in pioneer mood and in strengthening moode. I especially thank those who have helped me many times.
On the other hand, we new users should also think of a way to contribute to our community in one way or the other: either on the technical level, organization level, or financial level.
Just some general thoughts and sorry not directly related to your questions.