You can only have 1 person lv you up, so if you had done it with Trald, or Xav, the other 2 won't.
Gen only has 1 hangout event in the neighborhood, so I'm assuming you mean the one where you meet Boss. Did you start a new game, or did you load a save file then clicked update. You don't need to have met Boss to see him yelling in the neighborhood.
You're encountering Blood in the gym but he's not paying you any attention when he's working out because you don't interest him, so it's not the long event as if you were or if you're following the wiki. I don't think anyone updated the wiki. It's a fan made one so you'll have to wait till someone updates it. He also has a different scene in Ferron's hangout seen as well when you do.
Thought I fixed that... Wonder what's causing it to act up again...
I should really make an faq about systems in this game. Thanks for the idea.