It is a complex problem, what you are really discussing is how the entire education system is designed and the incentives in that system.
Fundamentally Trump is running on what kind of country you want America to be and in particular its societal make-up.
As a successful businessman the current situation is very favourable to you and I don't see why you would vote to change it. You can get access to good people at competitive rates (the best in China and India ~2 billion population). Taxes in the US can be managed quite well as a high net worth individual.
However many people in the US are not in your position and do not like the direction the country is heading in. They don't agree with large scale immigration and being undercut by immigrant labour. They feel the country is losing its identity.
In relation to your issues: Hillary Clinton will result in more of the same policies. Trump is opposed to common core but you are right he has not given a detailed policy position on education. Trump is a candidate that will 'shake up the system' or at least try to. I have no doubt that the US workforce can be improved and better educated but this is not something that the president can change in four years. This requires 20 years planning with good policies.
Trump is a man who appreciates and rewards excellence and is more likely to implement policies that allow the excellent to succeed and not be held back. Who is more likely to agree with the following book?
This is pretty much the argument that Charles Murray makes in Four Simple Truths. He suggests among other things that testing services have a huge potential market in testing and certification for occupational, rather than college, fitness. It's an interesting, arguable book