Agreed.
Agreed.
Agreed. (Leaving out philosophical concerns of stopping to question things 
)
Maybe.
I don’t think you are being strawman intentionally … maybe you are missing the point, maybe I have miscommunicated it somehow.
w is not about contextual menu per se, but well established keystroke that is followed by some other keystroke for very popular functionality within Blender for given context where w is called in the first place.
Let me put it this way.
Do you agree that contextual menu holds functions/actions that are most helpful for given context?
For example in edit mode you will get probably most popular actions that are done with meshes.
My specific example to illustrate the point is that mesh context menu holds subdivide, but you can replace it with any other popular action that is or will eventually be included in the context menu and is not accessible with other dedicated shortcut.
Assuming that you have not misinterpreted my OP then I have to assume that your comment holds belief that context menu belongs to right mouse button exclusively. Thus - in edit menu to do some popular action with mesh (i.e. subdivide) user has to press right mouse button and then do keystroke for that action (i.e., s). Or maybe choose yet longer path and actually after right clicking navigate with mouse to action (i.e. Subdivide) entry in the context menu GUI.
My argument is that context menu (which is simply holder of list for popular - relevant, curated, and agreed on by Blender devs and users - actions that are tied to the context) apart from pressing right mouse button should also be accessible by keystroke. Thus
right mouse click - keystroke or
right mouse click - navigate with pointer to action in menu - left click
should also be able to be achieved (which IMHO is much faster) with
keystroke - keystroke
in order to execute an action. If user is mouse guy, he/she can move through menus and shiny icons with pointer. If user is blender oldie where w’ing is way of life 
or someone who discovers that muscle memory keystrokes win, he can do popular actions for current context with keyboard.
Don’t you agree?