To be fair, in an American high school it's unheard of that you would continue on to 10th grade if you failed any of the core classes in 9th grade, let alone 12th grade... I literally would not have believed it possible. Maybe there are other cases like this, but I wouldn't have believed it yesterday.
So they're hit with an utterly unprecedented level of incompetence by the school, and she's a (single?) mother working 3 jobs. In that situation it's perhaps not surprising that the oldest has the least supervision among the three.
I guess I'd just disagree that "staggering level of entitlement" is the correct description. I only see a depressing result and a family that's in a very complicated situation, and is rightfully angry at what just took place.
Sure, teenagers should take some degree of personal responsibility, and parents for their children, but in a situation as complicated as this one, I personally wouldn't try to make that judgement from the outside.