I had installed a drain in my rudder. It always dripped until the temperature went below zero. Probably leaked in around where the shaft enters the rudder at the top. I didn't have clear evidence of other places where water was entering. As long as your drain hole seals well for the summer, it's got to be an improvement over leaving the water in the rudder (where it will freeze, expand, let in more water next season, and slowly cause damage). My water leakage was brown, and I became concerned, and eventually replaced my rudder.
In the end, upon destructive inspection, the bottom 25-30% of the interior was quite water logged. It didn't appear that other areas of the rudder/foam were damaged or degraded in any way.
While you can't tell too much from the outside (unless you see freeze/expansion cracks), but in the end, my rudder would probably have lasted many more years. The failure might have been the bottom breaking off from accumulated water damage (corrosion of the inner structure, delaminating, foam saturation).
One other possible test: Expose the top of the rudder shaft/quadrant. Grab the quadrant and push/pull to see if it moves up or down. If it moved "up", then your rudder is negatively buoyant. If it moved down, then it is positively buoyant. Before replacement, my was negatively buoyant, maybe by 10-15 lbs. The new rudder is positively buoyant, and floats easily. Because of this, I have a new metric for monitoring for future water intrusion .... when it no longer floats, it has absorbed water!
On a similar note, upon receiving my new rudder, I immediately removed the factory caulking around the shaft, and with a dremel, enlarged the space/cavity for the caulking. I made sure there was lots of room for caulking and that it could bond well to the SS shaft. This is where there would be flex, and if I ground the rudder, this is the area that would most likely open up to allow some water ingress (aside from fully damaging the bottom on a rock!). This is a fix you could do to an existing rudder by dropping it ~6 inches and working on it.
Cheers
Chris