I’d have worked with the Blannie (Black Annie) idea. Set it in Baltimore during Zero’s regime, where this scrappy young orphan exposes the epic-level Demonrat corruption of the city that leads all the way to Zero himself, and he goes to prison. An epic chase scene through Baltimore to D.C. where she’s attempting to be whacked by Loretta Lynch, Elijah Cummings and John Lewis for trying to break the deathgrip the Dem party has on the Black community.
She’s then rescued and adopted by an up-and-coming Presidential candidate named Donald Trump and goes to live in the White House and helps lead uprisings across the nation by the Black community against corrupt, entrenched Demonrat machines and eventually becomes the first Black woman President, Annie Trump.
Heh. Interesting way to set the story in "modern times" and make Annie black, while being faithful to Harold Grey's original intentions.
But I would prefer to have Little Orphan Annie as a period piece (set it PRE-depression for the first film, it would be the year 1924 if they were following the launch of the comic strip), with a little curly haired redhead protagonist.
The supporting characters, if they were accurate to the source material, would have plenty of "diversity" and include Daddy Warbuck's bodyguard Punjab (an 8 ft. fall native of India), his Asian-American driver The Asp, and the mysterious God-like figure Mister Am, (the first two of which would probably cause politically correct liberals to go into meltdown mode because "people of color" are servants).