One,
Would you agree that despite whether or not the machine did X only or moved in on an angle, you would be lined up perfectly IF you could sync any point on any individual pass perfectly? Or would you have to then know which pass you were on and trig out the X and Z to get back to your original start point and add or subtract those values in your tool wear compensation?? (Maybe it would be only one or the other, getting late, can't think...) If I'm thinking correctly, that would be the real trick to it ONLY IF the machine in question cut in on the angle and not just a new X diameter per pass...
(I'm kinda stupid when it comes to proper terminology, lol, bear with me
.)
If that's the case, it's still just a matter of building the holder to self align during any particular pass. The only difference being a little bit of trigonometry involved if it wasn't the X only variety.