I conjecture that much of the legitimate pain from checked exceptions in Java were because the language to talk about exceptions was so limited.

For instance, consider fold or map functions. There was no way of saying "this might throw anything that might throw", so the only option was "this won't throw anything and that cannot throw anything" or "this might throw anything".

Without the necessary flexibility, developers aren't "forced" to consider only error paths but also manifold impossible paths that aren't easily distinguished from legitimate error paths.