Is it possible to compare rolling friction with sliding friction? For example if you measure the sliding friction for a standard chair on a smooth floor and rolling friction for a rolling office chair on the same floor, can you then compare the two? Or would that be comparing apples with oranges?
It depends on what you mean by rolling friction.
There is static friction which enables the wheels to roll without skidding when the chair is being pushed, and there is rolling resistance, which is sometimes referred to as rolling friction, which would slow down the chair when rolling on its own because of compression and decompression of the wheel material when rolling.
In either case they are distinct from sliding resistance (sliding friction) which occurs if the maximum static friction is exceeded or if a wheel somehow locks up so that the wheels skid.
Hope this helps
There is friction between the wheels and the ground at the point of contact between the two. If the wheels aren't skidding, then the wheel is stationary at that exact point (even though the wheel as a whole is rotating, the exact point of contact is stationary), so the friction will be static friction. There will also be other friction in the chair. For instance, the connection between the wheels and the rest of the chair will have friction, and that will probably be kinetic friction.
When you push a chair that doesn't have wheels, you will have static friction at first, but once you apply enough force to get the chair going, you will have kinetic friction.