Samuel you're right in most of your reasoning. But most companies now have a policy of supporting the 2 latest previous versions. For example Facebook already announced they'll be dropping support for IE8. Google I think will do so as well.
So right now IE8 and Android browsers are bigger nightmares, I know that, but I think on a longer term, when IE8 and Android Browser are irrelevant (they're starting to be already) Safari Mobile might be the one that gives us headaches.