Condensation I doubt would be anywhere near as bad as oil with the past season's wear particles, moisture, fuel dilution, etc. You buy a new car or truck, it could sit on the lot for 6 months easy before being sold with the same new oil in it. So the fall is the best time to change it. For outdrives, and outboard lower units, same thing, if water got in during the season it could crack the housing if it gets cold enough. Plus, if you got water in the lower unit, you will see that when changing the oil and get it fixed over the winter in the slow season, not in the spring rush.