Thank you for your assistance. I have given up on using the radiant project as it stands. I think it is one of the most promising CMS systems around, but that it just hasn't been maintained in a useful manor.
In short, as a full time ruby on rails developer it is much easier for me to roll my own system, and add in the features I want then it is to patch these current extensions and so on to get "close to what I want."
I think Radiant was a super important part of making rails what is is today, but my hope for it was to launch a simple, maintenance free site that required less work to get running then building my own from scratch. This was accomplished for a public facing site, that just held content, but now that I need a feature not in core, it's just not the right tool for the job.
While this is a "Radiant" problem, I do not think it's a problem with radiant. I think the rails bar has been lowered enough for me (and many other developers) to the point that it's simpler to "roll your own" then to fix dated extensions. This is perhaps why so many of the extensions are out of date. For example Making a CMS from scratch that has the features I want for this hobby project, 10-15 hours. I have spent close to that already, looking for extensions, and trying to get other extensions (not just member login) to work. And Simple password while it would technically "do what I need it to" is still just http auth, and not a full session.
I think radiant is a project to keep my eye on, and be aware of, but right now adding a gem to a gem file and bundle installing is easier then installing an extension, and instead of a system that I have to train my self to use, I can just use all my rails in a new system with less effort.
All of that said, I do still think radiant has a place for CMS based content, where all of your features are "core" features, or are in supported plugins. Sadly that is just not the case in this instance.
Thank you again for your help, don't taking my ranting to negatively. I think radiant is a great project, and certainly one of historical importance. Just not a good fit for me personally in the place I wanted to use it.