@DavRE: Is there a way to have the actual "Ship Date" as a column field?

No.  I suspect changing it to work as you want it to, and changing all of the logic on many reports where it can be included, would be a huge change. It would be like changing the Due Date or the Terms or other fields that apply to the entire transactions so that they're applied to each line item. It'll probably never happen, IMO, especially as Intuit reduces their emphasis on Desktop and tries to push everyone to the Online version - where reporting is a dismal mess.