Doing Inlay with my Shapeoko

You’re barely giving yourself any room (half a mm) for error with the numbers in your first pic.
Most likely your Z-zero is set a bit too low. How are you setting that zero? Does your 30° bit have a flat at the tip.
The bottom one looks good. When you clamp that it’ll be nice and tight.

Check Community challenge #5: V-carving (closed) - #58 by neilferreri.