IANAL
Case 1:
Bootleg board.
Jurisdiction: Federal, international who knows
Case 2:
Operating any gaming machine.
Jurisdiction: State, perhaps city/county
For my state, there was no block on the operator license form to identify if the game was a pool table, video game, skeeball or pinball game let alone a block to identify what was running inside.
Of note:
In your area, you may be required to have a sales tax permit, operators license, location license, pay per machine. Annual renewal fees may apply.
My take away after looking for my state is that there is no way to identify on the form whether it is freeplay or not.fact If you don't give the man his cut, he is going to take you to the cleaners. conjecture The only way I see a business having these is as a loss to attract customer. informed opinion
I don't know what the law was before arcades got big, but no wonder they aren't now.