Thanks guys, I’ll try with some different bits. I know it’s possible I just need to find the right combination of blade + feeds/speeds so that I am cutting the wood without pulling at it.
The curvature isn’t a huge problem. I’ve found some workarounds. I basically create a separate 3D model that only has pockets for the areas that need to be checkered and I remove a little bit of material from the surface.
Original model on the left, Model for the checkering pattern on the right:
From there I do a finishing pass on the model to the right and set the stepover to the desired width:
After that I make a mount that will hold the stock at the correct angle to do the final grooves.