I am wondering if there is any way to properly model the heel-toe cutting effect or an endmill with the Solid Sweep Cut?

Here is a look at an example of what I'm trying to model. This is the preview of the solid cut.

Basically it is just a flat end mill being swept through a part on an arc. But when you look at the faces created:

The geometry at the beginning of the cut is incorrect, as can easily be seen by showing the solid body I used to cut overlaid with the model.

The cutter overlaps with the model after the cut! Has anyone had any luck trying to make this type of feature geometrically accurate? This seems like the whole point of the solid sweep to me...

Thanks for any help you can provide!

Some info:

SW 2015 SP3.0 / Windows 7. Follow Path was on; the same geometry is created with all the options, except for "All Faces" which fails...