For the villain's plan, I take it Senshi is thinking about attacking or invading the school at some point since he's got cameras trained everywhere. Is that the angle?
As far as what the gang is saying they're interested in, I figure it'd be that they'd want to expand their influence. I guess they would have somehow heard about the amount of heroes that Senshi has taken out (the gang's informant wouldn't know they're still alive tho, so the gang assumes the heroes are dead). But they want to work with him and/or contract him to help take out heroes in their sphere of influence in a mutually beneficial arrangement (Senshi gets paid, they get more freedom for their crime). Unless you're thinking of going in a different direction.
Also as far as my character goes, I'm thinking he'd ask Senshi for a job and he'd ask him to infiltrate the school. I thought of a side character yesterday that would be a great for just this purpose, who'd disguise Kono so he could sneak in. As far as what you'd want him to do, I want to know what you'd think!
BTW if you want to do a role play with me i do:
Dragon Ball Z
Anything to do with assassins
Anything to do with demons
Anything to do with angels
Anything to do with demons and angels
Creepypasta and if you made you own, wow
(and any other anime or manga) Warning: IF YOU WANT TO DO A ROLE PLAY WITH COLLABORATION OF OC'S THEN WE MUST DISCUSS THE CHARACTERS,SETTING,ORIGINS AND ETC. Thank you and goodnight