Since we are building the app in PHP, we should probably use a PHP based CMS. I am familiar and comfortable with Drupal and Wordpress from the PHP CMS world. Either of those will work for me. If you have another recommendation, I will listen.
The other questions...
We need to distinguish between accounts and account types as well as users and roles.
Accounts are the main entity of the system. All items, offers, connections, communications, etc. go to and from accounts. Furthermore, each account is uniquely identified by its handle (display name).
There are three account types: individual accounts, business accounts and swapgroup accounts. There are differences in what each account type can do.
Items Connections Help Needed Resume
individual Yes Yes No Yes
business Yes Yes Yes No
swapgroup Yes Yes No No
As you can see, all account types can create Have/Need Items (the classified ads) and manage the connections related to those items. Business Accounts can post "Help Needed" ads (the Job Search component) and Individual Accounts can post a Resume displaying their professional skills.
Users & Roles
Users are the people who manage the accounts. Individual Accounts are managed by only one user. Business and SwapGroup Accounts can be managed by many users, and the users can have different roles.
Owner Manager Member
individual Yes No No
business Yes Yes No
swapgroup Yes Yes Yes
The Owner of an account can manage all aspects of the account. They can enable/disable/delete the entire account, they can modify the account information and manage user roles as well as manage Items and connections.
The Manager of a Business Account can not enable/disable/delete the entire account, but they can do everything else.
The Manager of a SwapGroup Account can not enable/disable/delete the entire account, but they can do everything else.
A Member of a SwapGroup can Add/Remove there own items within a swapgroup.
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