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In principle, I think the idea of language being misleading is tightly intertwined with the the tension between expectations that people have in their experience with a given application of language (i.e. reading a written work or having a conversation with another person), and their actual experience of the language application.
I also think that the concept of learning is also important here. Over time, people learn to better understand or use applications of language, so what may be misleading at one point in time for a particular person may not be later on.
In order to be motivated, I would like to have a good idea of the impact the work would be making. I would like to see a clear explanation of the process taken to come up with the question and a list of who in LW supports this question as being an effective target of attention at this point in time and why. Maybe this could be documented in the question post and maybe there could be rounds that potential questions to go through for community members to vote/discuss/rate them. Maybe there could be a backlog of other questions that have not been chosen yet with reasons why they have not been chosen yet to help new questions arise. I would also like to know which other LW users are working on it (to avoid duplication of efforts) and if there are good opportunities for delegating work among multiple community members.
I like the idea of sub-questions. It might be interesting to have a display in the form of a graph with vertices as question/answers and directed edges as indicating a sub-super relationship between questions/answers. I think this would help us get a big picture view of the progress made and how it was achieved.
Since there is only so much that can be done by one community, I think it could in some cases be useful to have questions that are intended to be handed off to external parties like academic groups or certain organizations or renowned individuals after we do enough investigatory work.