So I started this question by asking it of Kake and Bob saturday morning then got busy and couldn't come back to it until now. There are lots of questions about why more people don't use the guides and I thought it would be helpful to look at we as admins use the guides we run. Most of us seem to use it as a form of extended memory (There was a good pub|bar|restaurant here). This is probably why most people would use it, and really we need to figure out ways of making that easier and more accessible for people.
For me personally the Guide is a hobby that helps me get in touch with the city I live in. I wasn't born here, nor did I grow up here so I found that working with the guide has made me more aware of the local history and space than I would have been otherwise.
I think right now the issues we have is that more people don't realize that they exist. The project as a project is in a period where we're ... not stalled ... but resting a bit. Taking our Guides out into our communities is as far as I can see the next place to go. The current issues facing the guides aren't technical as far as I can tell, but a social. How can we (as admins, and power users) get more people adding to the Guides?
-Chris