Dave,
I think it very possible for water to get back into the crankcase...but that was not the case for me. If you look at the pump diagram, you can see two seals separated by a spacer washer (part numbers 9, 10, and 13). The spacer ring is positioned between the water seal and the oil seal and is aligned with small openings in the pump body. I have no idea of design intent but it seems likely to me that the small openings in the pump body were intended to allow the leaking fluid (either water or oil) to drip/weep from the pump so that it could be easily detected.
When my pump failed I saw the drip, drip, drip from the bottom of the pump cover plate...making me think at first that I had a leaking cover plate gasket. Only after using a small mirror and looking up at the pump housing (behind the pump cover plate) did I see a corrosion trail leading from the small openings in the pump body. My guess is that if the oil seal failed first the same thing would happen but the drip, drip, drip would be oil instead of water. Whether leaking oil would work its way back to the starboard motor mount as you have described is another question.
Perhaps other pumps for other engines only have one seal between the water and oil sides of the pump. In that case it would be more probable that water would enter the crankcase when the seal failed.