I am not an aero engineer but this is how I see it ...
Once a plane enters compression, drag, I believe is not in the equation anymore cause you have already accelerated to the compression point. Its not how fast you are going, but at what point do you lose control to change your angle to stop the compressed state.
Once into compression, there is nothing that will slow the airplane down or change its angle outside of the normal control surfaces.
Some planes, as mentioned, had special control surfaces (outside of ailerons, flaps, and elevators) that helped break the flow of air over the wing and slow the plane down or kept the plane slow to the point where the normal control surfaces worked.
So if the speed at which compression starts is greater than the speed at which the control surfaces no longer work, your plane is now trimmed for that angle and you will continue your downward flight path until terra firms interrupts it.
I would assume that the steeper the angle at which compression begins, the harder it would be to maybe naturally pull out of a compressed situation.
If your control surfaces are only good up till 100 mph and you enter a dive that brings you to 150 mph, your screwed. If you cannot somehow slow the plane back down to 100 mph or below, at the angle that you are currently diving, you will lawn dart.
That is how I view it ... I could be all wet.