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Since air will be at the top of the cyl, how will it bleed out the bottom?

The bleeder valve has to be at the top or air will not bleed out.

In a conventional system the bleeder is on top to let the air out. If you bleed the cylinder with pressurized fluid, the fluid overcomes the air and it will be forced out. It doesn't matter whether you bleed from master or screw, the pressure moves everything in the system. My brother has been using a simple garden sprayer for years. He always reverse bleeds, simple effective and works every time. or bleed the cylinder and flip it upside down. I'm not arguing I'm just trying to think outside the box!

When my buddy did his conversion 15 or so years back he mounted original style cylinder bleeder down. Simply unbolted it and turned bleeder up and gravity bled.
Worked for him.