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I agree that combining 2D and 3D is not easy and more a quest for the right way.

In Blender V 2.79 there will be a new kind of plug-in, the shadow catcher, making it possible to match the perspective of a white plane with an existing background picture.

The 3D object placed on that plane will cast a shadow on the white plane.

Using the alpha channels the white plane will disappear leaving only the shadow casted in the right perspective on the background picture.

It does exist already but I never tried it before because of a lack of time ect...