HELP! Physics Ladder to follow path [Pic Included]

Hello, I have a problem on my hands that I just cannot fix, nor find any tutorial that teaches me to get what I want to achieve.

I have a bookcase ladder that I want to achieve these three things :-

  1. Only moves when player (or physical force) is acted upon the object
  2. When moved, follows spline and stops due to friction
  3. When reaching the curve of the spline, to rotate away from the spline so the ladder follows the curve of the pole.

Pictured explanation below,

I have read a lot of tutorials on what I feel is relevant and even tried Itween but to no avail, all the help I can get is very welcome!