There's no doubt (in my mind anyway) that English is weird and difficult; annoying (at times) and illogical. Possibly because I was a bad student at school in my teens, I have never properly understood the whole issue of grammar, parsing sentences, past participles and all of that. However, I have always had a fascination with words, their meanings and their origins, and I think it's English that has led to that interest.

Other languages also have their problems. I learnt French at school (and did a few years as an adult too) and never got to grips with the genders of nouns. Why is a table (furniture) feminine for example? How is it possible to remember them all? I still enjoy attempting to speak French nevertheless.

You point to the deficiencies of English with regard to the meaning of "free". Absolutely. That's a shortcoming. However, many other languages have their own idiosyncrasies. I worked at a university with a campus in Kuala Lumpur, Malaysia. Bahasa Melayu, the local language, has a very different grammar compared to English. See https://en.wikipedia.org/wiki/Malay_grammar for some aspects of it. I remember having conversations with Malay speakers, suggesting a English way of expressing a thing, to be told that that was pretty much impossible in their language. This led me to believe that English might be more subtle; though perhaps on the other hand it's more suitable for circumlocution, evasion and indirectness!

At school my French teacher was also an advocate of Esperanto. I wonder if that sort of language was what you had in mind instead of English? I don't know enough about its benefits to judge, but I wonder if a constructed language can really be as rich as a "natural" evolved language - even with all of its clutter and detritus.

Thanks for your comments - they really got me thinking.