I helped my brother move a pin out of a guy's house in the dead of winter. He lived in a lake house, and it had a very long walkway to the back of the house. But the first challenge was actually getting it out of the basement. It was a Black Hole... while the machine breaks down, it's still an incredibly heavy cabinet, and the stairs were cellar style and icy.
He was a nice guy and he had shoveled the recent snowfall thinking it would make it easier for us. What that really does is creates a nice slick surface to walk on. It was a precarious move, but we made it without anyone getting hurt.
At my old house, I had a difficult staircase to get to the basement - a 90* corner at the top of the stairs, and a very narrow landing at the bottom that meant lifting the machine over the rail. I eventually gave up on that. I decided to get machines in and out through a window. That window was about 4' high, which meant some creativity in getting the machine to height. I purchased a high-lift hydraulic cart. From there we would push the machine out the window and onto a convertible dolly laid flat. It worked really well, and I was able to do it by myself in a pinch.