In reality, we grossly overfeed our captive snakes; I doubt that they would get to eat even once a month in the wild (could be wrong though.) I think that it's more possible that we can overfeed them, than to underfeed.
I think that even in young, growing snakes, overfeedng could be detrimental. The digestive tract of pythons has developed to digest one big meal at a time, not several smaller ones in a week. I know that also, with overfeeding, gas can build up in the digestive tract, in the spaces between the food items, and cause the snake to bloat. I saw an overfed BCI like that, and it is not pretty.