Some of the manuals were never finished in the first place. For example, the Tips & Tricks guide still has many "TBD" sections and is watermarked "Preliminary".
The new "Manage Names" features have not make it to the guides, so I doubt other features have made it in there.
As a more experienced user, I would rather they focus resources on fixing bugs and moving on down their development roadmap. For newer users, however, outdated help material can be confusing and detracts from the company's image. It just doesn't look professional.
In the past I've suggested using a Wiki and letting the community help with keeping these up to date. But that raises questions of the cost and time to host and manage the wiki, fight off vandals, etc.
Also, folks often do need offline access to help material.
What I think would make a lot of sense is put the manuals into Skydrive or Google Docs. Looking at the formatting Skydrive may make more sense. Google Docs is still better for allows larger groups to simultaneously edit, but you have to make sacrifices in formatting. I've use Skydrive to group-edit some very complicated and highly formatted Word Documents and it works very well, though it does have more of a learning curve if the participants are not MS Office savvy.
What I would recommend to LWD is identify a small group of long-time, highly supportive, and knowledgeable volunteers to update the documentation.
LWD can then easily save the updated Word Documents to PDF and put into RW.
I don't know how the manuals are currently updated. If they can only be updated with a software update, there is still likely gong to be lag between new features being released and manuals being updated. Still, it should be easy to add a link to the most current "draft" documents on the web, which you can still download.