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1. About 5-10psi is plenty.

2. I usually just dump in a bottle and keep bleeding until it is gone. Brake fluid doesn't really have a useful shelf life once you open the bottle so I just put it all in. If you are trying to replace all of the fluid then use 2 bottles.

3. If you go for the 2 person method be very careful to make sure you close off the bleeder valve while there is pressure in the line so no air gets back into the line.

Yep we were good. I got the chamber up to about 10psi, but the tube going to the car's fluid resovior still had air in it....is that normal?

No problem - the only problem is when there is no fluid in the reservoir and air goes down into the brake lines.