[ERA Chas]

Dan,
I'll put this as politely as possible. Your simply killing yourself for no reason. It ain't that hard.
Here's what worked for me for 3 decades-and yes-even starting with an empty system.
As I said in the other thread, get speed bleeders. There's NO reason not to have them. You will thank me. Open once and close when finished. They're tons cheaper than all the other stuff you put on the car. Order them and take a break 'til they come.
While waiting for them, order a vacuum bleeder set. Pick your favorite and just do it. Mine came from Griots 2 decades ago and is still perfect. Made in Switzerland. Get what ever one he offers now.
Then-forget jacking a mile high and forget pedal-pumping. With the car up but level-open your new speed bleeders and fill the reservoir. Let it gravity feed and run out the open bleeders, checking the reservoir. If none runs out-don't sweat it.
Close the bleeders and one at a time, put the fitting from your new bleed hose on the 1st open bleeder with some antiseize-not dielectric.
Connect your compressor hose to the vac canister and (with a full reservoir) begin to pull fluid through the line. Have your helper watch the reservoir and add fluid as needed. NO PUMPING.
Do this 3 more times and you have a rock hard pedal and no air. And it won't take more than a pint of fluid since you already have fluid in system. Then do the clutch bleeder the same way.
Think your pads are away from the rotor because there's no fluid pushing them out or the pistons are corroded to the bores.