What I do is go off the weight of the pot. So before your next watering, when you know it's dry (when you 2 knuckle it and it's dry wait an extra day or two, or till the leaves start dropping, to know its really dry) lift the pot and acclimate your arm(s) to the weight of it when it's dry, then water till partial run off. After you water again acclimate your arm to the weight of the pot when it's fully saturated. That way all you have to do is come in to your grow room, pick up the pots (now I also record the day I water and start to realize that it's USUALLY dry after X amount of days but I still check the weight), and if they are light enough you know it's time to water. No having to get your fingers dirty and no guessing.
Also, to directly answer your question, if you over-potted then it would be more difficult to tell when to water, yes.