Thanks for sharing your file. I have taken a look at what you have so far . Everything looks to be "In Computer" and "Wear" for cutter compensation in the first machining setup group (4 4), it looks like all of the toolpaths are missing geometry in the second setup group(5) .
It has been my understanding that "In Control" will always put the tool center point on the defined geometry (MasterCAM, SurfCAM, Fusion 360 ETC..) unless you add stock to leave, then the software offsets the toolpath by the amount you define. "In Control" is a fairly "Old School" way of programming. Back in the day when they didn't have powerful computers and software (early stuff like: paper tape punchers , tape readers and manual input) to automatically calculate toolpaths offset by the radius of the cutter. They programmed everything in absolute values and then used the machine controllers to offset the values using tool length and radius offset tables.
The only thing I see that is a little off is if you change the cutter comp back to "In Control" for the contour you shared in the screencast. and try to simulate it. The strange part is that when you generate the toolpath and look at it everything looks fine. But once you simulate it and show the toolpath with the simulate settings the generated toolpath seems to move to the outside of the part rather than where the defined geometry is. This is something i would ask the Autodesk Team about to clarify if it is operating correctly or if it is really a bug.
Zak Welsh
Zakary Welsh Machine LLC