Quick google of the artist, it's obvious why she'd be selected for such an honor: Amy Sherald has said that her art has changed since she moved to Baltimore. Before her oil paintings were autobiographical, but now her works have taken on a more social context, exploring identity and the roles of race and gender in life-sized portraits.
Being totally honest I looked up some of her work and I really like it, but I wonder if anyone checked whether she was just a good artist, or a good artist who paint portraits. She has a couple of self portraits that don't really look like her, if I'm being honest.
The strange thing about Michelle's portrait--beyond it looking nothing like the subject--is the artist typically injects lots of color in her art, 3-4 bold or pastel colors in each work...why is Michelle's so devoid of color? It's strange, it's like she's only partway done with the piece, nevermind it not looking at all like Michelle.
Barack's is strange, he gets lost in the color a bit. It's a striking painting but to me, why would an artist choose to drown the subject in a literal forest of color when that subject was the President of the US...wouldn't you want to convey that gravitas and import in the art? I'm no fan of his politics but Obama was a great orator who inspired people, I don't know why you'd show him hunched in a chair being overrun by the forest, it's really weird.