Best way to do it would be load up three dispensers with random stuff and build a three piece randomizer (fucking huge circuit) and pay the "dealer." Dealer pushes a button, randomizer goes off, 1, 2 or 3 is selected, item poofs out.
With the /money pay option, or even tossing an item as payment, would suffice, money would go into local accounts (National, City, whatever). The nice thing with items is that we have a gold/diamond regulated economy is that they have a physical value based out of the Terraferma Market.
So if anything, I highly doubt, based on the Java and MC "rules" of cooperation that they have, you can't have a random integer (item) come from a chest, though, like I said, a RAND3 circuit hooked to dispensers would definitely do it, though it has to be player manned.