I actually think you're better suited with the Turbo Dream or Subculture instead of the Happy Hour. You'll get more use out of a directional twin than a true twin for your ridig style and usual conditions. And no, you shouldn't have trouble transitioning to a higher end stiffer board. If anything your riding will get better as the increased stability will inspire confidence.
Go ahead, drink that kool-aid.
FS: Forum Sauce 142 $200 plus shipping
FS: Flux SE30 $75 plus shipping