You just spit in the face of every "less fortunate" individual who worked harder than everybody else and did catch up. It makes his accomplishment seem rather worthless. After all, he could have simply accepted the charity of someone like you or supported a system where that charity was systematically dispensed. Why bust your ass and work hard?

Oh, that brings me to the next point. Incentives. You just killed any incentive to work hard and bust your ass if you're in the "less fortunate" group. Why bother? You can just wait until someone helps you up.