> I really think a semantic facelift would

I think you mean a syntactic facelift, without changing semantics. You mean making the syntax look more like TypeScript, Kotlin, or something, right?

I suspect overhauling the syntax is the kind of change that the committee would see as rather dramatic and with limited payoff. Introducing an optional alternative syntax alongside the existing one, would likely be seen as opening the door to syntactic inconsistencies, more likely to harm readability than to enhance it. The Python community has a relevant saying: There should be one -- and preferably only one -- obvious way to do it. [0]

I don't think it's a serious problem that Ada uses and then rather than &&, and uses or else rather than ||. It's the kind of thing you can get used to with time.

[0] https://www.python.org/dev/peps/pep-0020/