Re: Issue with bleeding the brakes
You say your mate is opening the bleed screw(s).
If you haven't successfully got one wheel done, preferably the right rear, IIRC the others should remain closed. If you allowed the fluid to drain from the calipers when they were off, it could take a bit of fluid and time doing it by pumping the pedal.
If you have no success working with even one wheel, and you've checked for leaks, you might want to rent a pressurized brake bleeder from a local parts shop.
Hopefully somebody with more recent hands on experience than I have will chime in.
If you need a shoulder to cry on ...
... pull over to the side of the road!