I know I am late to reply but filling a tube of that length would be more brake fluid than filling the cup and pouring it in..
You start furthest away and work to the closest. I also do the cycle at least twice. You should only press the pedal enough to build pressure back up after opening the bleeder. Hold the pedal down, loosen and tight the bleeder. Was it a clean squirt, then move to the next. If it was weak, bubbly, etc do it again. move to the next wheel.