There's still have a chance you will lose, no matter after win or lose, but with higher win chance it will increase a possibility of your roll number hit the target (specific number like >50).
You can do all in one if you can afford to lose.

I think you should use "goal amount" and "limit amount". Goal amount means your profit amount, how much you want to reach the goal amount in your schedule gameplay (don't play greedy). Limit amount is the fund which you can afford to lose (again, don't play greedy).
That's will help you to manage your gambling activity.