Breaking the documentation down into smaller pages would help. It would then be easier to create a table of contents for each page including the subject matter of each page.
It would also help users who want to help with the documentation - we wouldn't have to hunt through hundreds and hundreds of lines of code to find a grammar or spelling mistake.
I liked in the past how each page had a link to edit the documentation page you were currently viewing - it definitely made it easier to suggest improvements.
I'd suggest migrating the documents to a Markdown format. The current language is similar to Markdown, but I've found it dissimilar enough at times to make it difficult to figure out what exactly to do to make my changes.
Finally, I'd suggest starting over with the docs. The number one complaint I see is the documentation. That would lead me do believe that the current documentation is broken (or at least not ideal) a tool to encourage adoption. Don't get me wrong - there is definitely useful information in there. However, I think the documentation needs to be restructured - or at least the structure needs to be re-examined. Trying to hold on to a legacy structure (ie: the current documentation) will only hamper the necessary changes that need to happen. Certainly the current content can be used, but it may need to be chopped up and re-arranged to make it fit.
As for what version? I'd say the version to next be released whenever this project gets going. If v2 is 8 months away, make the documentation for that version - there's no sense building documentation for a version that will be obselete 1 month after the documentation gets written.