I just wanted to follow up here for any of the CNC guy's who may have looked at this.

THe answer was "not possible with the type of machine and tooling we have. Here's a quote from an experienced machinist that was working with me on this:

"there is no way to produce this part with a corner rounding endmill. Like he stated in his recent post, there is no way to have the tangency point be correct all the way around the circle/oval. Even with two tool paths, it won’t work, due to the ever changing radial drop caused by the cylinder and the perpendicular hole through the middle of the part, the radius would only be tangent to one surface at a time, except for the 0 and 180 degree positions in a quadrant.
Even though a corner rounding endmill has a one to two degree lead in/lead out for the radius, there is no way to properly follow the hole and radial drop on the cylinder od without losing tangency of one or the other. Like he said, even if you could “match” two paths to produce the tangent points, the radius would not be correct. It would change size in each quadrant. It would start the correct size then decrease as it move to the 90 degree position on the quadrant, then start to increase again as it move to the 180 degree position. With that being said, it would produce more of an oval than a true radius. "

Tech Talk!!!!

The only thing I have left to wonder is if a "True 4th axis software" (Something I dont have yet) and cutting a "Specialty tool", Can I make it work.

The answer and followup to this is not for the MoI forum though.

Thanks Michael! I've added "Subtended angle" and "Rolling Ball Fillet" to my knowledgebase!