I started a vision resource late in 2018, and didn't have much time to contribute to it, but I did give it a bit of thought. I've copied the main points to start discussion and brainstorm, and hopefully we can take some of this from "vision" to "implementation" this year.
Some ideas I liked from the past:
Identifying quality content
Seems like this is still an issue. There were some good ideas here. I also like the idea around Wikiversity:Featured, and I'm also looking at some of the templates, such as and Help:Resources by completion status in particular. I've always felt a little discomfort with the "completion" notion, as it seems like creating learning resources is a race with a set distance, and in a wiki you could always have a new contributor add new information. I think the idea of "ready" is good, and there are obviously points where content is "in progress/not ready".
There is an "ad" banner for me that reads "Learn how to contribute to Wikipedia during Contribution Month". While I'm all for cross project promotion, why are we pushing people to contribute to the big project and not here? (I know this is likely a WMF/all project ad, but we should be advocating to get in this rotation). I'd love to see that space promote content or explain how things work.
This is all just a start. the 2009 outline was huge and very ambitious.
We've had Wiki Campus Radio and the Sandbox server in the past -- these were really visionary type ideas, and things to get excited about. I think they are both still doable and practical, but will there be any audience? Would something else be better for engagement or learning?
To add to this, I think I'm going to pick one of these projects to do. I have waves of free time and no time, and this past month has been too much of the latter. I'm going to solicit some comments at the Colloquium, as this resource seems quiet (and I need to put in a bit more work before it has community relevance)