Jon,
You are right, and I periodically get into deep and meaningful conversations with various colleagues on the points you raised in your original posting. Unfortunately, I have been wrestling with a totally different set of problems lately, and have not been able to translate "what we need to do is..." from the conversations into "what I have done is...". Soon, I hope.
WRT Simon's suggestion, you might get more from the Diagram Slide Show topic in that Model Views section. Basically, what Simon is talking about is having a set of diagrams illustrating either a developmental progression or a set of perspectives (with and without elements relating to a particular perspective). Each time you run the slideshow you draw in the current diagrams - that is, they always represent the latest saved changes.
Bringing in Paolo here, those changes will have been made manually, and the Model Views facilities would either be telling you that the diagram has already changed, or there have been developments in relevant objects that now need to be (manually) added to or removed from the diagram, depending on what you set up in the SQL search views.
I'm getting out of my depth here, but maybe it would be possible to create an Add-In or MDG technology that performed specialised searches, opened relevant diagrams and updated them automatically.
There is a possible role for a series of shortcuts too - it seems to me that there could well be a meshing of different EA tools and facilities here, but I just don't know how it would all work. And THAT is where we return to Jon's point about "what I want to do, how I could approach it, why these EA tools and facilities might be useful, and then what steps do I actually work through". This is the sort of area that the white papers are supposed to address, so maybe we should look into them.