RE: Question 1: School to work

I do not see how we can morally NOT measure student success.  Whatever we may think our education system is for, when students leave school unprepared for work or for further education, our system has failed them.  Of course there are other contributors to failure (family, economics, social forces), but these remain statistically pretty steady across the years, so we should be able to see, with good data, how our schools serve, for example, students who complete their HS diploma with those who do not, students who do so with good grades, with those who do not.

Also, the problems with defining success are not insurmountable.  If it is challenging, well, then let's get to it.  Some factors for measuring success are easy, but discussion and brainstorming (and probably some trial experiences) can get us to a well-designed system;
>  of course, income is a pretty good measure
>  employment level is another
>  further education (>3 units per semester or quarter) is a measure that would constitute success in lieu of income or employment

We can start there and go on.