The yes/no questions are throwaways, might as well get rid of them.
Under promises "Stop __________" could be... stop immigration, stop Muslim immigration, stop losing, and a lot of other things. Way too open-ended. You could change the clue to something like "to end this 2010 piece of legislation".. and the answer should be the Affordable Care Act. Or how about "repeal and replace ____"... that would be easier to get.
I recall the "part of the beauty of me" statement now... but... the guy is so in love with himself that could be a lot of things, too. I tried "I'm very smart" and some variations.
Conway has said lots of stupid things, alternative facts isn't exactly a catch phrase she just said it once.
Maybe take "Baron" as a type-in for Barron?
I tried just "Trump" for the Trump Organization... that one seems like a bit of a throwaway question as well though I didn't get it because I wasn't sure what you were looking for.
Siblings question- too easy to guess. Another throwaway.