What does Estimated Market Value mean and why do my prints not go from highest to lowest?

The Estimated Market Value is the value that your items are guessed to be when sold in the aftermarket.

Why doesn't the pricing follow the order of the lowest prints?

Because that number is subject to pricing, odds and other factors in play when the print was initially issued and sold as well as aftermarket sales data for that print and others like it.

Are all of the items listed worth exactly what they say?

Award items may not be accurately approximated as they are closer to priceless and sell for much higher listing prices in the aftermarket reflective of the difficulty the owner had in earning the award.