Diaz probably wins R1, though I think it could be a good fight. Tobias is stronger based on feats so far, but Diaz has more showings against skilled fighters (Tobias is definitely supposed to be trained, but Diaz scales higher). Stats make this a difficult fight for Diaz, unless he gets better stats showings in future episodes
Gang war, probably Diaz again, by virtue of apparently just being able to buy off anyone he wants (as annoying as that is, imo)
Round 1: Richard wins IF and only if Tobias doesn't grab him at all. If he does then Tobias is gonna kill him, the man was knocking around painkiller for fun and punched Lala across the room with a single hit. He's also a black belt and he stomped the green light enhanced street fighter.
Round 2: Tobias probably. If he really has taken over the old lady's position then he's got connections on top of connections. Additionally he's got black lightning weaponry, the 100, and resources equal to Wilson fisk. If only Cyanide wasn't dead he'd have his top lieutenant too. Plus he has the ability to create more people like painkiller.