Once the bolts are freed up, dropping a rudder is not that difficult. Copious amounts of PB Blaster and lots of heat can convince the bolts to give up their death grip on the quadrant. The issue is aluminum quadrant, SS shaft, and SS bolts. If you do remove your rudder be sure to use lots of Tef-Gel on the bolts when it goes back together. Also if you have a gas engine, the heating part can get tricky or deadly.
The problem is that nobody wants to leave the boat on the travel lift for the amount of time it takes to free the bolts. Once the boat is on stands, the rudder can't be removed ... the tip is a mere inches off the ground. I suppose the key is to free up the bolts before getting to the travel lift ... ah, there's always something that I'm not particularly anxious to do!
Gunni, my rudder is 32 years old and presumably in the water every season for its life (except for maybe the season before we purchased her). I see none of those signs. The only thing I've ever noticed is a tiny amount of clear water seeps out of the leading edge seam and only for a day or two after haul-out. I can see that the seam is open slightly at the top, at the shaft, but nothing dramatic, just a hairline opening. The rudder has been scuffed at the tip and I notice clear water leaking from the scuff for an equally short period. It has always appeared to be dry before we have any freezing weather. I've never drilled to drain the rudder, nor do I particularly want to. Even though it is painted the same red as the bottom paint, I've never noticed any heat that would be considered alarming, even on a sunny day. I can't see anything unusual from year to year and we've had it now for 12, but I don't know what I don't know about this rudder and that is what bothers me.