Everybody's system is different.
If I am brewing a brew with an OG > 1.060, I can sparge, keeping the water above the grain bed until I have collected the required pre boil volume.
For a brew with an OG > 1.055 and < 1.060, I need to stop adding sparge water before I have collected the required pre boil volume, but I don't need to top off with water.
For a brew with an OG < 1.055, I need to stop adding sparge water when the gravity of the runnings drops to 1.008, and then top off with extra water in order to get my required pre boil volume.
These are guesstimates, and may be slightly off, but they are pretty accurate for my system.
Your system may be very different than mine.
As far as continuously monitoring the gravity of the runnings, as Yooper said, you don't need to do it at the beginning of the sparge, it's only towards the end that it becomes important. I use a refractometer to gauge the gravity of the runnings which is quick, easy, and accurate. You could also use a taste test. If the runnings taste sweet, you can continue sparging. If the runnings no longer taste sweet, then you may want to think about stopping the sparge.
This is obviously not as accurate as taking a gravity reading, but if you try it for a few brews and concentrate on determining the gravity by the sweetness of the wort, it works pretty well. (This was what I used to do before I got a refractometer.)
-a.