When I mentioned my buddy using his thumbs earlier and deleted it, it was due to the statement sounding confusing. My buddy could bleed the master by pushing the master with his thumbs instead of using a large screw driver etc.. Sorry for confusion.

Ok here is where were at. I diagnosed into the late hours last night. A new master and booster will show up today in case we need either.

Master on the car removed last night to check to see if it was bench bled correctly. It appears to be bled correctly. Plugged both ports with fittings, put in the vice and can easily push the cylinder in and out with a screw driver and see steady line of fluid pushing up into the port of front and back.
Also removed the ports and got solid streams of fluid shooting out of both ports.

While master was off started the car and pressed the pedal to check booster with pressure applied to the rod. It appears to function as it was intended by still has a very loud whooosing sound under the dash. This sound is literally louder in the car then in the engine bay.

adjusted the road to within .20" and put everything back together. When master was removed I plugged off lines with rubber plugs to limit air intake when rebleeding.
Bled lines again and did have a little air which was expected from taking it apart. Solid, very solid fluid at all four bleeders. Pedal feels hard at this point when not running but fire it up and a loud very easy pedel pressure to within a 1/2 of the floor,(or about 10% of the pedal throw) and it does actually hold brakes at that point. That's what I have and I have no idea why its doing it... Stumped and never run into this issue. So at this point I have one more night to try a few things and then we leave in the AM as is. So if you see this Cuda rolling in you may want to step back.... LOL. Thanks for all the help!