I think Henry will allow some ground-shaking moves, if Bloom thinks they are called for. Henry is the wallet. If Bloom convinces him we can be a top competitor, next year, I think he'll open up the wallet and okay bold moves.
The thing about trading Vaz, JD or Bogey is that those trades will likely save money- perhaps just temporarily, but nevertheless, money-savers. If Bloom wants to trade Bogey- the biggest fan darling on the team- I think Henry will go along with it.