Hi Aureus, hi folks.
I agree with you that adding a few bells and wistles to the dimensionning and annotations in SketchUp (SU) would probably not add too much to its price.
Maybe that can be a feature of SU Pro, justifying even more the 495$ vs 0$ for the free version.
My only fear is that some people will want more ways to draw rectangles and then circles, and then arcs, and then polygons and then ... etc.
All of this is very valid and I would like them in a Pro version as long as its price don't go up to far from the actual 500 $ (approx.) value.
I don't need, and I am certain that many others also dont need, another AutoCAD or Catia with their zillions of icons and menus and sub menus, etc.
Wait a second ... with dozens of plugins, SU's interface begins to look like Catia and other complex software. OK, I said nothing 
Lets evolve, but not too much at a time. Lets keep SU looking simple if we want it to appeal to a lot of people that are not necessarily savvy with 3D and CAD. So, yes, a free version with a decent set of tool and a Pro version with a more complete palette. Both of them able to grow with the help of plugins.
Again, these are only my ideas.