I see what you're getting at here. The part your getting confused about is PSI, so forget about it for now. Power requires a certain amount of air and fuel no matter how it is being produced. This is a constant, give or take some for air temps and other factors. The fuel and MAF system limit your hp no matter what because the more efficient blower moves more air to make that power. Does that make sense? So yes you could slap a Whipple on at a PSI low enough to keep your MAF from pegging which will still be around 500hp.
This subject does seem a bit confusing. rwhp is clearly different than engine hp. Spinning a blower reduces the rwhp available, so my though was with a more efficient blower, more rwhp would be available. Consider a turbo setup with no drag on the crank....it frees a lot of hp because its not robbing power from the engine. The engine hp is limited by the injectors and MAF, but rwhp will change if your blower (or turbo) does not sap as much power from your engine. This should be the case with a Whipple. Also, IAT2 temps should be lower giving you more real world power due to less timing being pulled in the summer weather or after a pull through the gears.
Some folks may want to swap to a Whipple (lower boost) first rather than building up the Eaton. Then, if they want more power...change pulley, add injectors, MAF, clutch, etc.