Twan, try and wrap your head around the following simplified explanation. Don't over think it.
The regulator is simply a variable restriction. You can set the regulator for 0psi all the way to 100psi, and all you are doing is changing the flow rate of the restriction. It doesn't matter what pressure you set it at, the entire system from the pump to the regulator will operate at the regulated pressure. After the regulator, you have free flow and thus little to no pressure.
UNLESS there is a fixed restriction in this system before the fuel is getting to the regulator. This is a HUGE pump relative to the demands of the engine. Even at WOT high load, the OP is seeing the 100psi. before the heads. That means there is a restriction greater than the restriction created by the regulator somewhere between his fuel block (forward point of measurement) and the regulator (final point of measure).
It's more like water from a garden hose than air from an air compressor. The air compressor regulator regulates what comes off the tank down to a set pressure. But a water hose, you turn the valve on full blast with a spray nozzle and the spray nozzle regulates the full flow. In this case, it's like the valve is only slightly open, so all the pressure is behind the valve (restriction) and your spray nozzle only gets a trickle of water.