Dealing with intense complexity of the new Administration Menu

Between 6.x and 7.x, the Administration Menu has grown much more complex, to the point where we're now dubious that it provides any benefit over the core static menus for the client users who'll be responsible for maintaining our sites.

Equally worrisome are the fact that there are now 12 top-level items (up from 7 in 6.x), which is about 4 more than the maximum recommended in most usability heuristics ('5 plus or minus 2' is the usual recommendation), and the fact that the menu is organized in multiple levels under multiple new categories. In practice, I find it necessary to scrub much of the menu to find the administrative option I need to use, and am struggling with a way to help users get a conceptual map of how it works. Generally, drop-down menu systems only work well when people can maintain a mental map of their organization, and this one is too complex for that.

I see that in theory we can change the structure of the menu at example.com/admin/structure/menu/manage/management. In principle, that could partially address these problems. So I have questions about that:

1. If we restructure the menu, will our changes persist through upgrades to the Administration Menu module?
2. Assuming the answer to '1' is 'yes', what happens when new items are added to the menu - where do they go? Do they create new hierarchies? Do they selectively restore the old structure? Do they simply come in at the top level?

If restructuring the menu isn't an option, what's the chance that the menu structure will get a usability overhaul?