I need someone to hand-hold me through the process.  I really have a very limited budget for the project (things are tough all over, I know, I know) which is why I'm looking for a mentor rather than a developer.

The site will likely have to be rebuilt from scratch.  It currently uses a custom cms. the database is mysql. It's in need of a major upgrade any way.

 I was thinking of switching to joomla unless there's a better cms for our needs. I've got MAMP and joomla installed locally but I know just enough to likely get myself mired in problems.  I've done some research and found some modules and components that meet our needs and several acceptable templates. but I'm not sure. 

the site has public areas and two classes of log in - workers and clients. 
Clients log into individual pages of media (audio, video, photos and documents) that have been posted specifically for them
workers log into their individual pages which contain their upcoming schedule. contains a messaging area and an upload interface for large files.  Individual schedule items contain specific information, media for downloads and directions to the specific work site.

the admin side allows upload of media, creation of public pages, client pages, jobs, work sites and scheduling of workers to jobs.
    some features are not functioning correctly.