Timing - When the plant is actively growing and not stressed by mechanical or chemical injury. It should be well watered and happy with the weather/temperature for a month.
It is better to spray again when the plant has stopped responding to the herbicide (as in trying to grow again). At this point it is weak and beginning to regrow (in a favorable environment). Most herbicides will have this time listed as 2-4 weeks.
The recommendation is pretty common on most professional herbicide labels because that is how systemic herbicides work. If you want a kill, it only works when the plant is moving the chemical through the plant. If/When you apply something that stops this growth, applying more or early doesn't help as much and tends to be a waste. It also is advised not to pull weeds as the goal is to keep the ai in the plant and affecting the roots. If the plant is pulled, there is less leaf tissue for the ai to be absorbed by on a following treatment and the roots might be able to survive and grow another day. The following treatment is likely only to work when the plant is using up stored energy to create new growth. The best time to reapply is when you see it trying to grow anything green again - to introduce more into the plant along whatever new path(s) it created or is using to survive.
I have successfully painted leaves of Quack grass growing inside of bunch of ornamentals with successful kills. After about 2 weeks, it finally turned brown, and I ended up just pulling it. Never came back in the same area.
I have also killed off established Bermuda grass without Glyphosate. It takes 3-4 applications/months, but you can't do it in a season because as you slowly kill it, you have to wait for favorable conditions (regrowth) to treat again. This usually means it actually takes 2 seasons (maybe 3) to fully remove Bermuda grass (without full renovation/solarization/glyphosate).