Armen
We too have had this and it is not serious and no damage has been done. The paint is simple latex and you can dry it and repaint. We have repainted seversal times. As for drilling a drain hole, i would not do that as you could drill through the hull. I doubt that this would happen but why chance that. So, no worries. As to the leak location, it could be....
The mast seal, this can leak and run to there, had this....
Chain plates, maybe, but then it would be behind the hull liner and may not get to here...
A port window, leaking and running into here...yes, had this
A deck hatch does the same...had that
A leaking water hose or sea water hose to the head
So...taste the water to see if it is salt or fresh, then look for he source
Hayden, on anchir in Block Island