Hey Bro,
I think we tend to over water more than we think. There's been times when I've neglected(by my standards) a plant by ignoring when I think it needs water, and by doing that, I actually make the plant healthier by doing less, hence the "less is more" approach. Cannabis is a rugged form of plantlife....Remember that you're working with females here, and even though they're plants, they're still woman... they like the 'bad boy', 'treat me like shit and I'll respond positively to you' mentality. hehe!
It takes a knack figuring out what the right amount of water is and how often. You need to factor in the container size and the amount of root development thats occured. So a plant that's just been potted up to a larger container, there's a lot of dirt with no roots, so when you saturate the soil with water, it sits in there a lot longer.
In my opinion, you want your plants to be a bit cramped in their container. An extreme case of a bad idea would be planting a seedling in a full 5gallon bucket of dirt. You see people do it too. People say, if you stick your finger in the soil and its dry up to your second nuckle, its time to water. Bullshit. It's that kind of advice that we take to heart and end up with sick ladies.