Hi wmcfall,
For question 1:
For the work order screen, you need to make sure that you set the filter to show “All occurrences”. That will show you all of the Work Orders that belong to all users.
In the calendar, you will be able to see all of the users that are assigned to the admin. To be able to do that, in the Calendar tab, click on the Change link and check off all of the users that are available for you. Since you are the Administrator, you will be able to see all of the users there. Once that is done, you can see your users’ calendar on the right hand side.
For question 2:
A work order can only have one Assign To. On the work order list though, you will only have one person listed as the Assign To. You can thought, add multiple employees as team members and have a leader who will then become the Assign To for that work order. This concept of team members is for time tracking purposes and it will not show up as multiple entries in the work order list or calendar.
I hope that helps.
Ronen