What workflows are people using for making dimensioned plan drawings of a 3D object?

Initially I tried using the Dim tools directly on the 3D object, but discovered that I couldn't do things like getting a Radius dimension for the diameter of a hole drilled into a non-planer surface (like a radial hole going into the outside diameter of a cylinder) because the edge that I'm trying to dimension isn't planar, and so the Radius tool can't figure it out.

I also had problems when trying to dimension directly on 3D objects because I needed to make a bunch of duplicate objects with each being rotated to present the correct face in one ortho view. This got a little confusing like when I had to make a design change what with deleting all the 3D duplicates and trying to align the new rotated 3D object with all the existing dimensions.

I tried getting all my views off of one 3D object using the built-in ortho views and changing the cplane, but it turned out that I couldn't control this well enough to get the particular 3rd angle projection relationship between views that I was aiming for.

Another problem I had with the 3D approach was that dimensions would get buried inside the 3D object because of where I was snapping or there would be Z fighting even in ortho views. So I'd have to manually pull the dimension objects toward the camera.

So, now I'm trying out make2D where I rotate the 3D object and make multiple projections from the Top view by rotating the object each time. The problem I have now is that the projections aren't accurate enough to play with the Radius tool. In other words, Radius won't recognize a projection looking along a fillet as an arc.

Has someone figured out a nice way to make a drawing with multiple views and Radius dimensions?

- Peer