Retiring comfortably with a five-hundred-dollar-thousand investment portfolio combined with monthly Social Security benefits is entirely feasible for many individuals, provided they maintain realistic spending habits, moderate lifestyle expectations, and live in areas with a manageable cost of living. Utilizing a standard four percent initial withdrawal rate yields approximately twenty thousand dollars annually, which, when added to an average Social Security benefit, can comfortably cover baseline living expenses, housing, and healthcare costs for retirees who have eliminated major debts like mortgages.