Master cylinder first, then closest wheel first is how I was taught.
Factories place a device on the master that uses pressure to push fluid through, and collection devices to reuse what goes out with the air. You can make a pressure system out of a cap, a baster, and some fittings to hook them together. Still a 2-person job but it's done in 30 seconds. It can be a solo job, but 2 people make it easier. I use a peanut butter jar with fittings and such in the lid and a low pressure regulator to control the flow.
Fill the jar.
Hold the modded cap on the cylinder.
Open the valve to purge the air.
Close the valve (cylinder catches drips).
Put the cap on the cylinder.
Open bleeder (with clear hose to catch can for waste).
When peanut butter jar is almost empty close bleeder.
Release pressure from master back through peanut butter jar.
Put cap back on cylinder.
Takes 2 minutes.