Hello Steve,
You are able to find more information about how to create milestones through the following article on our Wiki:
http://usermanual.clarizen.com/#4-8-1-1-creating-a-milestone
And more information about how to create a task, click here: http://usermanual.clarizen.com/#4-9-1-1-creating-a-task
For the other requirements , I suggest you consult with Daniel Cohen, your account executive to discuss the requirements for the POC.
Regards
Eran Fishov