Yes, there is a legal issue: what you describe is illegal. Gambling is illegal in your state, other than state lotteries and tribal gaming. Any time you have consideration, chance, and a prize, you have gambling--so any time someone pays something ("consideration") for the opportunity to win something of value ("prize") based on chance (e.g. "randomly select"), that would be gambling, which again is illegal in your state, which in turn means you would be committing the crime of offering illegal gambling. You cannot offer people the chance to win money based on random  selections or drawings without running afoul of the law.