Use a deep-well 6-point socket with a long extension so you can position yourself exactly in line with the bleeder and it will come out without breaking.
As for your bleeding problem, I do not know why this is, but I know it is: When you begin bleeding a line it is almost impossible to get the pumping process started unless there is back pressure on the line. Once there is some back pressure the system will begin to evacuate air from the master cylinder's actual cylinder back into it reservoir*. That has to happen before it can pump fluid down the line to displace the greater amount of air trapped in the wheel cylinder. At the wheel cylinder you will never be able to remove all the air behind the wheel cylinder unless you have a functioning bleeder, it simply can not be done with the bike upright.
* You can watch this happen when you first begin to bleed the brakes, its the little bubbles of air that come up into the reservoir from one of the two little pinholes in its bottom.
