I would like to know if Apple Server is right for me.

I am the owner of a construction company that manages multiple jobs. What I would like to do is have a server set up that allows tiers of access. To explain further I would like to have 4 levels of pw protected access. In decending order there is Owner, Superintendent, Project manager, and Sub-Contractors. Each would need to be able to upload important documents to the server such as submittals and recipts. I would like the server set up so that I have access to all of the files from each section. In addition, I would like the Superintendent to have access to all files below him, Project Manager all files below him, and Sub-Contractor only files he uploads. Basically permissions going downward. Also I would like to be able to set up where each would have log in information so that they could access the server. As this is a small company in the scale of things it would be nice if each job had only access to their information. The company wide address book and calender would be nice as well and ability to access them via their iPhones would be great as well. Can anyone help me with this?

What do you mean by cumbersome?
I mean that it will take some data entry and testing, but that would be true in any case.
Also how easy will the interface be for the people trying to upload?
Very easy, as long as they're on your local network. The server will appear as an icon in the sidebar of any Finder window. They'll click to connect. After they enter the username and password the first time, it will be automatic.

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