Let me add a bit about "play time"
I am thinking of the workshop as aimed at people who are thinking of being the first person at their school to use WebWork. Thus I want things to be set in terms of the MAA hosted model, with some comments along the lines of "talk to us in a year, after you have run a course, if you want to build your own server."
I think the first point should be automated homework instead of a comparison of systems. (For teachers, that is the conceptually important issue. brand loyalty is much later.) I have a dummy class set up at MAA
where I have a bunch of logins. In particular, for X going from 1 to 24, I have adminX, studnetX, and taX. passwords are the same as logins.
Workshop participants start by logging in as a student and working at a simple assignment on product rule. We discuss as we go so they can see the student experience. Natural questions on grading and equivalent answers come up. Form the front projector, I have two browsers, logged in as a student for one and as an instructor on the other. I demo the process of sending an e-mail to the instructor and then receiving it and responding.
A second play assignment is to pick some topic and create a simple assignment for the students.
A third topic of play is roster management. I point out the file used to create the roll, but I comment that for the first class you do, it may be simpler to type.
Part of the theme of my playtime is that while I can see a lot of things I could do with WebWork, my first goal is to do routine drill work with my students and to get them to do those problems. That first goal is pretty easy to accomplish and worth the effort. Other goals can be faced on another day.
For implementation plan my recommendation is the following path:
1) Have a single early adopter use WebWork with MAA hosting for a standard course. (College algebra through calculus.) DO not plan to write any new problems.
2) When you have the experience of getting students to do routine problems without having to grade them yourself, smile and comment to colleagues.
3) When you have a few more faculty interested than can be handled by MAA, look for a server site in your region and see if they will host a few courses for you. They will probably say yes.
4) When there is some momentum talk to administration about the advisability of using a rival institution to host services for your students.
See if they will host a server for you.