Brian,
I agree with your plan to condense the guide down. I would still keep some parts of the Getting Wine chapter and put it at the end of the introduction, or possibly at the beginning of configuring wine. I agree about changing it to be mostly a reference to the relevant parts of WineHQ. Would it be duplicitous of me to just go ahead and redo the Getting Wine chapter and leave it as it is now, and perhaps merge it into configuring/introduction once you're done?
That way we'll have 4 chapters: Introduction Configuring Wine Running Wine Troubleshooting
The running wine chapter eventually needs to be rewritten too (outdated switches, etc.) It could probably be reorganized a bit to read nicer as well (for example, directions for uninstalling programs are given before running them.)
I'd like to have the documentation revamped by the next release. Combined with the coming winecfg patches, the major red marks at http://www.winehq.org/site/todo_lists can be replaced with happy green bars. I think we can easily have the yellow bit for the User Guide finished by then too. After that, the only major things in the way of 0.9 seem to be the developer and winelib guide, which are a bit beyond my abilities.
(note: forwarded to wine-devel for further feedback)
Thanks, Scott Ritchie