True. The checkpoints are a fairly nice add, but innkeeper's may not be the best. What I think would be a good idea, is to have a teleporter. At each stage of the Obstacle Course, the player gets a Coin. Say you pass Stage 1, you would receive the [Stage 1 Coin]. If you fall you can then trade that coin into a teleporter who will take you to that checkpoint. However, it only has 1 use.
Also, I am willing to throw together a makeshift Obstacle Course such as this, though it would be very shitty : /