Teacher Request: View AS a student

I work at a Montessori High School. My kids are essentially self-learners, which is exactly what Khan Academy is great for.

But as a teacher the site makes it difficult to keep up with them as they all move at different paces. What has worked best so far is I create a "class" for each student. Last year I tried classes with multiple students but they progressed at different speeds, so it just didn't work well at all.

My problem is keeping track of their progress beyond the assignments I've given. I don't love the teacher interface. In fact, it drives me CRAZY because you're on the right track, but the UI doesn't easily provide insight into where each student is.

Here is what I really want...

I want to see a list of my students, then be able to click on each student and simply see the SAME view they see with some minor added functionality ON THE SAME VIEW. 

1) assign videos, exercises, articles, quizzes, etc with due dates. It should just be a checkbox, a date field and a save button. To unassign it, I want to just un-click the checkbox and save. 

2) The student should then see a date due on the same page. 

3) If possible, I would love to have it sum up the estimated time to do all the assignment, so i don't have to add it up in my head.

I find the current teacher assignment page is VERY hard to use because I cannot see what the last thing the student was working on. Sometimes they go beyond the assignments I've given them. In that case I don't want to slow them down, I want to give them assignments they haven't done. With a change to the user interface (number 1 above) I can see which videos they have watched and/or watch them myself as a refresher. 

Currently their assignments page is on a separate page from the topics. So half of them just go to the next topic and don't even look at my assignments. This is their fault, but with a minor change of the user interface (number 2 above) would help them succeed. 

These changes would take the place of the "assign", "scores" and "manage pages in the teacher side.

I am very happy to draw examples of what I mean and or make you a prototype HTML page with these changes.