My initial thoughts are that we already have a good start in MeasureIt (now shipped with Blender), although there are some issues there to resolve. It does a lot of what we want, but I would like to see some improvements. I am not convinced at all by the current “Measure” tools in Blender, because they do not dimension properly, or in accordance with accepted draughting standards and they disappear too often!
I show this image as a quick “What you can do” with MeasureIt, it also shows that the lines are too long in most cases and I had to work some Clock Magic™ to get the gaps between the object and the dimension lines:
The good thing is that MeasureIt will render these dimensions to an image, but you then have to Alpha-Over them onto the rendered image of the object using Compositor - not a huge headache, but it would be better if Blender just rendered them to start with. I used an orthographic camera for this to get a proper test render, this one above is just a screen render.
I am tempted, if you all agree, to make a new thread for this requirement - a “Let’s Add Dimensions to Blender” thread, which you can start @nokipaike and I will enthusiastically add my thoughts to. the correct term for this is “Dimensioning” not “Measuring” in my humble opinion, we should adopt this, if you all agree and I will contribute all my knowledge to it, being a past draughtsman, both on a board before CAD was invented and subsequently. 
This 2D drawing was produced with only Blender, MeasureIt and my own PDT tools. I got the line drawing by using Wireframe Modifiers and some “tweaking” - we still have a way to go to get this kind of output easily and intuitively, rather than by magic and lateral thinking.
Cheers, Clock. 