Step Up is one of my favourite pricing games but it had the same flaw as one of my other favourite games, Magic #, in that the game's prop/set did not help the contestant understand how to play the game - and in fact I think it confused the contestant due to the cash amounts displayed.
It would have greatly benefited from replacing the cash amount displays with a monitor to support the game's explanation. The monitor could've displayed 4 ascending steps with "Least Expensive --> Most Expensive" underneath it, along with the bailout cash total amount to be displayed underneath each step as they progress through the game (similar to It's In The Bag). The contestant's selections for each step could then be displayed with the name or an image of the prize placed on the top of each step.
I would also change the gameplay so that:
1) the contestant places all four prizes in order from least expensive to most expensive before anything else happens;
2) then, as each price is revealed, the contestant has the option at each step to either a) bailout with the prizes and cash already won, or b) to go on, playing for the next step and prize they already selected for that step, or c) to go on, but if they think the price of the prize on the next step is less than the price just revealed they are allowed to swap it with one of the other prizes that hasn't yet had its price revealed.
Given how long the game is for a four-prizer, I'd also consider just making it a cash/small item game. The above changes would make it play similar to It's In The Bag and Hot Seat where the pricing is done first, then the bailout options are the main focus of the second part of the game which simplifies it for the contestant and makes it easier for the host to build drama around the bailout portion of the game.