I've got stairs that are about 10 stairs up, landing, shimmy the machine 3 feet to the right, then 10 stairs up in the opposite direction. The landing is too narrow to use ANY sort of dolly.
I'm young and rent a couple rooms of my house out to guys my age. After 2-3 pins, you'll get a system down and it won't be too difficult. When I have people over, they freak out when they see my stairs. "You need to install an elevator!." "Do you take your games apart?"
In reality, from legs on in the basement to pin secured in the van takes about 15-20 minutes on average now.
You can do it!!
I like the idea of having a couple of friends. Allows someone to take a break every once in a while.