As you can see in these pictures our Song of India (Dracaena reflexa) is having some problems. I say it is too much water, while my wife says not.
What do you say?
This does look like overwatering to me. This publication describes the cultivation requirements in Florida as having high drought tolerance but should not be exposed to salt spray.
When overwatering occurs you get some leaf drop but you also stress the plant so it is vulnerable to bacterial/fungal/viral infections which are the source of the spotting.
You can reduce the spotting by increasing the light levels and decreasing the amount of water. Let the plant get healthy and it should outgrow the disease. Repotting will not affect the disease as it is inside the plant.
A watering schedule should reflect how much light, how pot bound the plant is and the type of soil. For a plant that is in very high light (unobstructed south exposure), moderately pot bound and a soil less mix no more than once a week with enough water to wet the entire root ball. It is more likely that watering every ten to fourteen days would meet the plant's needs.