I work for the business that I am creating materials for, which make it a little easier to gather this information. A lot of the above questions are included on the training request form that I made recently. This allows me to create a list of follow up questions for the first meeting that I have with the requester(s) and their SME's on any responses that were vague or I just need more detailed information to plan out the scope of their project. It's really helped me streamline my start up process and feel it has helped the requesters have a better understanding what really is involved to fulfill their request.