[andreasvc]

Esperanto was designed first and foremost to be learnable, it seems to be quite successful in this regard whereas it's not a strong point of Ikthuil (as it wasn't a priority). With "ought to have looked", do you mean in your own opinion, or are you referring to some of Esperanto's original goals? I always got the impression that learnability and ease of use were bigger priorities.

Personally, I don't have much faith in the idea that you can make people's communication more precise and concise by designing the language in a certain way, just as I don't think that politically correct language leads to meaningful change. This is simply because I don't believe than language can drastically change the way people think (linguistic determinism, strong Whorfianism). Esperanto is very similar to natural languages in its (im)precision, which might just be the level where humans naturally converge to if left to their own devices.