I can appreciate your original point, but this degenerated into naivete. The is-ought problem exists in (and was formulated for) natural language, and ambiguous formal languages are childsplay. There are further problems (ignorance of the consequences of reality being finite, misunderstanding the operative layers of interpretation) but these two alone are disastrous by themselves. Don't mix up convention with implicit substance. There's a very basic philosophical lesson you're missing, and I'll let you in on the secret: The labels aren't actually descriptions of any property. The distinction is indoor baseball. Notations, syntax, semantics. What you want is signal, and you can transmit that any way you want. Writing and drawing were once the same thing. Still are.

You are right, and that is precisely the issue. When complex logic fails, we don't usually blame the machine. When natural language fails, we as of late seem to be trying to anthropomorphize a machine that cannot be held accountable. As if understanding natural language suddenly means it understands morals.