This would have to quite sturdy, and would only be useful for particular jobs (heavy and sturdy objects), but for those jobs it could be very useful. However, would it be easier than getting a dolly? I don't know. I'd probably want it to be bigger, perhaps a meter in diameter.

If you stuck an axel thru the middle and attached a rope to it, it may be easy to drag it up steps or hills.

If you're using it for heavy objecs, the greatest difficulty could come from needing to distribute the mass evenly around the wheel.

So, you want a 55 gallon plastic drum cut down to half-size, with hooks and bungee cords inside to strap things secure...? I think I'd go with a drum inside the drum spinning on bearings, so the parcels inside don't get jumbled around so much. Outside drum rotates, inner drum just sort of swings gently... then again, 24" seems kinda small, how about 36" or 48"? The bigger the diameter, the easier it is to roll over obstacles like stair steps. Best of all, you could jump inside the inner drum and ride down when you're finished, instead of using the stairs...