My starboard side one always drained but slower than the port, however once I took the time a few years back to get out the picks and really dig it out, it drains much better the last few winterizations. I would not worry about the block rusting through, I have not heard of that happening even here where we are 100% salt water but it is possible for the heads to rust through behind the valve seat area. In fact when I took my engine apart (blown HGs) 2 years ago and had the heads checked, the machinist felt the cooling passages were getting eroded and if they re-surfaced the heads they might not seal against the new HGs, and that to me also suggests a loss of cast iron. So I went with re-man heads that gave the old 4.3 a new lease on life.
Just because your drain is clogged it does not mean the block is about to rot through. Now I have always filled up this engine (manually, after manual draining) with -100 marine af with corrosion inhibitors, not sure if this really helped, but then again the short block is 32 years old and run in salt, at least half that.