You likely won't get any answers or ones that are worth anything because it completely depends on your complete reporting environment Items 1, 2, & 7 have too many variables to predict and all of us -- from what I've seen here so far -- have different reporting environments and requirements.
Also, as you move forward you'll find some things aren't needed or take longer/shorter to perform or you find ways to automate bits of it. For example, creating a schedule takes mere seconds but getting the end user to specify exactly what they want and making it fit into Tableau's less than robust scheduling can take several emails or a phone conversation to iron it out.
It would be best to work with your sales representative. Also worth reading is Tableau Server: Everybody's Install Guide .