There are many things I liked about this post. It made me wonder how much the questions you are asking are on the minds of young designers who are in the first decade of their career, or if these are questions that only come to mind after working on enough projects to see frustrating patterns that have little to do with “the design” but that effect what goes out the door?
More broadly I’m reminded of questions of power. If the power to make the important decisions that ultimately define the design are in someone else’s hands (e.g. the group manager, the VP) then the organizational design suggests two main approaches:
1) designers need to be excellent at persuasion and politics
2) designers need to move into generalized roles (with more general power) to be able to create an environment where they can give the required power to designers, or, when appropriate, to themselves.
There is also
3) work, or hope, that the organization can learn to better support designers, but this hinges so tightly to the specific boss, rather than the deeper culture of organization, that when the VP moves on, some of the same work has to be done again, with a new management team (suggesting #1 is an unavoidable realization of the working world).
Do you see a #4?