Builder,
There are no easy answers to your question:
a) When the tips of the blades exceed Mach 0.85, you have a problem. You have to do the math to find out how big your rotor can be for a given fwd velocity.
b) More power = more speed, also more power = more weight = less speed. You have to do the math to find the best balance.
c) the faster you go, the control system evolves, to accommodate the attitude of the rotor disk (cyclic). This is an elaborate analytical task, so my comments on this part end here.
d) Drag on the airframe is a "minor" concern in rotorcraft design - I put it in quotes because it takes a backseat to the rotor design task. The faster the heli goes, though, the drag increases esponentially. Computational fluid dynamics are used to optimize the config for high speed.
The equations, as you can tell, are inescapable.
STF