Re: Which villain(s) should the reboot start with?
Film 1: Penguin, Black Mask and Riddler developing as a disgruntled detective.
Film 2: Riddler is the full-on villain; Black Mask has overtaken Penguin's empire and is going to war with Killer Croc for weapons running routes through Gotham's abandoned subway tunnels.
Film 3: Killer Croc, defeated by Black Mask's forces, finds assistance in the form of a large drugged-out looking heavy named Solomon Grundy. Grundy offers them a drug that will allow them to instant heal themselves; making them nigh invulnerable to gunfire. At the end we learn that Grundy works for Poison Ivy, head of a South American drug cartel.
Film 4: Ripples in Gotham's underworld have corporate heads with ties to the underworld worried. Enter Clayface, for corporate espionage on behalf of one of the businessmen, sent to expose Roman Sionis's ties to the underworld.
Batman is in there too. This is the sort of steady escalation I want to see.
10 Year Cheesehead