I was helping take the trash out recently. The paradox of regular trashcans on wheels is this. If you have the wheels on the same side as the handle, the weight of the trash tries to push the can back down from the side. However, if you have the wheels on the opposite side than the handle, you need to pull it down highly irregularly. So here I am trying to hook the trash can to a wagon or cart for physical convenience, and like the weeble it was, it just flipped it over due to drag.
I wish someone could make giant trash hamster balls so you could just roll the trash down a driveway like a marble.
Either way I'm going to have to bring the trashcan down. They're company trashcans and the area I live in doesn't accept trash unless they're in those. You can't just make use of a makeshift unless you want to wheel both an easy container and the trashcan down and relocate one into the other after you've reached the road.