I’m assuming that instead of casinos (which, given the situation today, are perfectly legal in many places as long as you’ve filled out the required paperwork, posted any required bonds, hired workers, abided by laws concerning children, etc., etc., etc.), you’re looking for an inexpensive and easy way to get the same kind of cash as a casino owner. Like a room full of skill game machines: pachinko, Skee-Ball, bingo, and others.
Maybe you could. You’d have to check local ordinances, though. And you’d probably have to make sure that any redemption for cash is done away from the premises where the machines are located, so it doesn’t look like your players are gambling.
A variation has been tried before: in the 1950s, there were bingo machines (related to pinball games). Like pinballs, bingos paid off in free games, but the free game counters went so high (who could really play off the top “prize” of 999 free games?) that it was simpler for the owner to “buy” the games back from the lucky player.
This buying by the house and selling by the player disguised the fact that the player was really wagering that he could post enough games on the machine to win (er, sorry, that should be sell them for) more cash than he put into the game to play.
In other words, gambling. And that’s probably why your idea wouldn’t work in the US: because bingo machines had a loose association with gambling such as you describe, they (and slot and so on) machines were outlawed in most American jurisdictions. Yes, a sales transaction such as you describe is perfectly legal, but if the machine itself is illegal to begin with…? Like I said, check local laws.
Assuming that you can legally operate with bingos, Skee-Ball, and pachinko according to your scheme, and you do follow any other applicable rules concerning operating a gambling house, somehow I can’t see the average North American gambler putting up with the inconvenience of going to a prize counter, selecting something, then going down the street to sell it. Much easier to try one’s luck at a slot machine (or similar) in a nearby legal casino.
In other words, your idea might not fail because it is illegal; rather, it might fail because North Americans aren’t willing to jump through such hoops when an easier legal alternative exists.
[Bingo machine information, and info on the legality of such machines, comes from Roger C. Sharpe’s Pinball (New York: Dutton, 1977), pp. 55-56.]