Booleans of drawings with pointy edges often fail

[kriho]

This is an observation that popped up again and again.
When performing booleans on drawing that have points edges, especially ones using arcs, I get strange errors.

Example with pointy edges:
studio.replicad.xyz

I never have issues when expanding the shape like this:
studio.replicad.xyz

Just so I know how to create reliable scripts, what is the thing that makes the points edges problemetic / how can I avoid the issue?