Leaves are indeed a challenge to railroads. I stalled on a train at work this past fall. 9200’, 8600 tons with two engines. Tried suggesting we needed more power, but was told according to the book we were good for 9700 tons, ok to go. I argued that I don’t care what the book says, I am telling you the conditions of the track and this power. Yesterday we had 3 engines and 6,000 tons, 8,000’ and struggled to maintain 12-14mph going uphill. So we went, and stalled out a short time later. A few crews later, and the use of helpers 3 times finally made them decide to add power and leave the power on the train.
I think using leaf blowers on the mountain is a great idea, as Jason, and Steve have said. The trick will be to blow the tracks clear of leaves, and to blow the loose leaves onto the downhill side. It will take a little time to make this happen, but honestly this type of full clearing could honestly be done twice in the fall and should be ok so long as care is taken not to blow the leaves from the tracks to the downhill side.
So standard gauge railroads or railroads that run year round do this? No, however they use a high pressure washer in November to wash the “black rail” off. It’s called black rail because the crushed up leaves form a literal black rail grease, and makes the rails extremely slick. For both pulling and braking. Not fun. But this is their way of cleaning the tracks of leaves. As for the drainage, some places have the option of not worrying about it till it’s an issue.