I agree that it does! "ß" turning into "SS" when uppercasing is awful.
>It feels like replying to some bugfix in, say, Ruby with something like "I never liked Ruby anyhow".
In this analogy, "Ruby" would be the German language. And in that case... yes, I can disagree with a bugfix if it makes matters more complicated! I can argue that something is a misfeature, like ß is. Removing it would improve the situation, especially from a technological viewpoint.
>German's not English, even though you might prefer if it was
That's kind of a low blow. "ß" is not a defining feature of the German language.