Misread the intent of the title... but since I'm here...
TYPICALLY, these sort of things were the most fun when I was working on the railroad (1:1):
(From my engine service years.)
* I typically enjoyed snowy days (when in engine service) if the engine had a good warm cab heater and my thermos was full of hot, black coffee.
* I typically enjoyed helper service (front or rear). When shoving from the rear, I loved the challenge of managing slack through the humps n' sags on the way to The Mountain or grade in question.
* I typically enjoyed main line running., freight or psgr. (Added bonus in that I enjoyed the additional challenge of psgr.)
* I typically enjoyed the "unpredictability" of railroading: One minute I'm switching in the yard and expecting to do so all day, the next minute I'm on my way to the sand and gravel plant to pick up several cars of ballast, then high-balling up the main for miles to help get a washout fixed that was washed-out the night before. (This happened several times in my stint with railroading.) OR, I'm working a local job... and next thing you know... I'm off to go help a stalled train up a grade. These sorts of things.
* I enjoyed the feeling of having done a job well.
I could go on, but you get the idea. Railroading has a lot of managerial BS that goes with it , but the real reasons those of us with railroading in our blood were out there was for reasons like the above.
Andre
