Matthew,
Thanks for replying so fast. I want to work through this with you to show you what I am experiencing. Take a very close look at the pic you posted and you will see that the origin for the insert is set for tip tangent and everything looks good. And it is good, but only if you want to use that insert in that very orientation and no other. Rotate your insert 20 degrees, see the origin is floating in space.
If on the setup tab you input some non zero orientation it will end in a fail for any insert weather you use a tool holder or not. As an example please select the 35 degree diamond insert and no tool holder. What you will see is the origin is not tip tangent even though that is selected and you have not even tried to rotate the insert to some other orientation. Then input an orientation like 20 deg. Now it is very clear this system is broken as the origin is again off floating in space. To demonstrate this, assume your new tool is usable and go and use it to turn the OD of a straight cylinder shaped bar. It will look kind of OK because the yellow stock shows it was cut away but look closely, the tool path is above or below the part!!!! Now post it out and look at the g-code. The X value will not match the diameter of the bar you wanted to machine.
As far as I can tell, none of these orientation options, custom inserts, custom holders or selecting "no holder" options work properly. Some look like they work but post them out in g-code and check that the code you get will actually cut the diameters and exact dimensions you are modeling.
I know this sounds like a strong or unfriendly post and I apologize for that, I am trying to understand this like everybody else. I know it is not your fault. And I also realize that some of this code may work, I just have not been able to observe it yet.
Cheers