Re: Which villain(s) should the reboot start with?
Don't think we'll be seeing Dr. Hugo Strange simply because Marvel will be releasing their Dr. Strange movie in the next couple of years. I would go with Christoph Waltz though.
Man-Bat, Killer Croc, too much like Lizard. We saw that in the Amazing Spider-Man. No need to see something similar in a Batman movie just a few years later.
Riddler, Penguin, Black Mask, Mr. Freeze & Court Of Owls should be the only options for WB, for the first couple of movies.
Can't kick off the reboot with a winter theme, because we just had that with Rises. So Freeze will have to be saved for one of the sequels. Black Mask could work as a side villain but not a main one right away...why? Will audiences accept another obscure villain (to a general movie-goer)?? One that has a mask covering their face where he has an even more limited use of his expressions. Just the voice and movements. At least Bane can use his eyes and physicality.
That leaves me with Riddler/Penguin/Court Of Owls.
Maybe Court Of Owls falls into that Black Mask category. Maybe it will remind people of the League of Shadows? Depends on how it's presented of course.
So it traces back to Nigma and Cobblepot. It's a good start anyway because everyone and their grandmother knows who they are. Marketing is easy.