Robert A. Heinlein suggested that one of the attributes of a successful society is a certain amount of looseness in the corners.
The contradictoriness of the English language (in which, as noted, overlooking and overseeing mean something quite different, whereas fat chance and slim chance mean the same thing) gives us all much to think about, even in ordinary discourse. Selection among multitudes of synonyms, and the occasional oddball word like chthonic, give English speakers a certain... flexibility. Rather poetic, in a way.
I've considered for years that one of the reasons English is successful over French is that, when it came time to write dictionaries, ours was compiled by a choleric, disorganized party animal, whereas the French appointed a Government commission.