So, this is actually my wheelhouse. I did Philosophy of Language in grad school (multiple grad schools) focusing on ambiguity and implicature.
The interesting issue here is that we have a reversal of the function of language. Language is effectively a complicated form of pointing at things: what is a "bridge" we can point at bridges where we agree. Here, we're starting with the word and trying to point at all the things that word applies to, hence we're doing it backwards. We'll start fighting when we get to the corner cases because the rule of "bridge" isn't meant to be stretched to corner cases. This isn't an issue in life because the function of jargon is to cover corner cases. It's all well and good to that thing on your skin a "mole," but when you're in the doctors office, it's much easier for them to adjust the precision of their language between a "common nevus" and a "dysplastic nevus."
Here again, we're just pointing at things with language, but the resolution is turned up. The language should be serving the concepts, not the other way around. When language fails us -- when we don't have a word for what we're pointing at -- it's trivial to coin a new term or adopt a loan word from another language.
In a sense, here, the reason legalese exists is exactly because lawmakers want to adjust the resolution to prevent these types of problems. Otherwise they the same process will happen, but it will happen in the courts.
For me "vehicle" means "a singular thing designed and able to move people around under it's own power or via a powering mechanism that people generate themselves" and "in the park" means "touching the park": hence the memorial is not a vehicle because it no long able to move people around. However I see the sled and the surfboard as vehicles because they are designed to move people under the power of gravity/waves.
My definition, however, is fairly arbitrary and not actually significant except to the way I communicate. J.L. Austin, if I remember correctly, wanted to create a Descriptivist dictionary where they would literally just go around regions and countries asking people what they meant by words... unfortunately, he died very young and the project never happened.
Where I disagree most with the linguists I talk to is that I believe that the concept of "correctness" is instinctual to language, insofar is people care passionately about prescriptive rules. I just think that we can be descriptivists, and see language as a map where people are arguing about borders. That we believe these borders real, and are "correct" or "incorrect" in our tribe is important to the usefulness of the language and our survival, even if they are ultimately entirely arbitrary. Thus, I've always speculated that an instinctual "correctness" value would show up, and we very much see it everywhere -- like in this game -- and the concept basically has to be unlearned by most people when they really get into learning about language.