I think the problem with Troy is that, even tho he makes dope ass music. He does not really "fit" in with this new generation of rappers. So labels are not gonna be fiending to throw a big bag of money at him. He will do Pusha T numbers at best.
What I think he needs to do is either link with a Def Jam or Interscope straight. And then just personally build his connections with Fab,Push,G-unit,Maino etc. And gun for being a Meek Mill type rapper. Who puts up 100,000 with sales. But has a strong following in the street, which will help him constantly get shows.
Any other method is gonna end up in failure. Troy will never be a hipster/backpacker/mainstream america darling.