The only way you will be successful at maintaining your weight once you lose it, it to make the permanent lifestyle changes and be totally aware of what you are eating and why you are eating it.
We don't reward ourselves for gaining weight and I don't see why you feel the only way to measure your success is by the scale and then to reward yourself with money. I can tell you now you will not lose weight every week and some weeks are going to be better than others. Much better to reward yourself for the lifestyle changes and the reward is good health and feeling better.
Am I wrong in thinking you might be a teen? If so, I can see you line of thinking better.
And one last thing, never ever reward yourself with food or food treats. Food is fuel for you body, not a reward, not comfort, not to be eaten because you are bored, etc.
HW 356 pounds - CW 131 - GW 137
Life isn't about waiting for the storm to pass. It's about learning to dance in the rain.