OK, cancel my drill press thingy. I kinda think finding a ready made solution is going to be tough but how about this (I'm assuming you are making the steps)?
- a piece of ply with standard casters
- box with bottom, 2-4 bolts through bottom
- attach #1 to #2 bolts but with compression springs between the two.
- sides and/or front back of the box almost to the floor
No weight on the box, it rolls easy; add weight and the springs compress allowing the box/step sides and/or front back to hit the floor.