Interesting thoughts on this.... First, I love this dream, but how do you create a custom plan for students? While it would create additional jobs, where is the money going to come from? This is yet another example where we don't want to be taxed, but we want the tax dollars to fund additional spending. The current system isn't the best, but we go over core subjects, which is necessary (to a point).
Second, the shortage of teachers comes from a few different variables. Some of it is being graded on students' standardized test scores that the students themselves aren't being graded on, so they don't care and it hurts the teachers. Teachers' salaries are hurting; however, back to point one, where is the money going to come from if we don't want taxes raised and aren't willing to pay for it that way?
Lastly, I see the point, I really do, but how would you implement this? How would you customize plans for hundreds of thousands (even millions) of students. Think of how many doctors there are. Each one spends roughly 30 minutes to an hour sitting down with a SINGLE patient so they can create a healthplan, refer if needed, for that patient. At best, you could create 8-12 (20 max) different teaching plans and take a class of students and separate them by personality, but with that you lose diversity, you lose great opportunities for students to learn how to work with other students, and you lose opportunities for other types of growth.