The 'Aggressive' approach is probably the most fun out of the three different approaches (the two others being the The Big Con and Silent & Sneaky) that the Casino.
Wonderama Arcade Grapeseed $1, Videogeddon Arcade La Mesa $1, Warehouse Arcade Davis $2, Insert Coin Arcade. If you follow this walkthrough you might be able to. The Silent and Sneaky approach to the Diamond Casino and resort DLC is probably the hardest you could do.
