My son began Flight Academy in the Fall of 2019. He was required by FAA to pass medical exam and cog screen all totalling over $8000 that we paid. Is this deductible?

Unfortunately, there's no provision of the law that allows for the deduction of these expenses.

What is allowed as he was required to buy computer, software, books, and expensive headset for school.  He is not going for his private but his commercial which would be an expense for his career.  Thanks

Also, will his tuition be allowed once he begins paying on it?  It will be deferred until 10/2020

If your son received a Form 1098-T for 2019 from the Flight Academy you will be able to receive a tax credit for the tuition, fees, and required equipment expenses paid by the student loans.

You do not be need to wait until you start paying on the student loans to take the tax credit.