Yes there is some air in the tube when you start, but multiple pumps clears it out and bleeds the brakes. Keep pumping and it will quickly overfill the bottle (much more comes out then goes in). A lot of guys use a vacuum, so yes that is another one-man option, I've also seen a tool that pushes fluid in but have never used one. Brakes are typically bled from farthest to closest to the master cylinder, right rear, left rear, right front, left front. There are a few odd ball cars out there that this wouldn't be the prefered order of bleeding, but in most cases its not overly critical anyway.