Ok.

First, he isn't a "self-made billionare".  He had heavy financial backing by his millionaire father through numerous failures.  A self-made billionaire starts from little to no backing.  Look up Gary Johnson (self-made millionaire), if you want an example.

He addresses nothing of the many transgendered members already in the military.

Many cosmetic surgeries are already not covered in military medical coverage.  A diplomat could negotiate to include transgendered procedures to be classified as such, so there would be no additional cost.  In fact, the military started agreeing to cover those procedures, but they can always change that.  That way you keep the transgendered/equal rights crowd happy while keeping costs down.  Trump called himself a "great negotiator".  He's proven he's absolutely not.