On stupider machines that are only 10s of thousands of dollars/euros/etc, you also have to be certain that what the machine expects for tool geometry matches reality (meaning that the correct tool was in the correct tool location, that the tool is mounted in the holder at just the right length, that the tool itself hasn't deformed, etc.
That said, I wouldn't bet against AI stuff potentially being good at generating tool paths in the future.
Sometimes I think that existing CNC stuff might be too dumb. Where is the lathe equivalent of auto-probing a 3d printer bed or using machine vision to monitor the print? Where is the mill equivalent of visual examining each part like a pick and place machine does? Why can't I put a piece of metal in a vise and just tell the mill to square of the ends? It could be that what I'm picturing is only stuff that casual users would be interested in, and thus there isn't sufficient money to develop it.