Want to avoid stress in retirement? Don’t overlook these time sensitive decisions — they could cost thousands if ignored

Core Insights - Turning 65 introduces significant milestones and critical decisions regarding health coverage and financial planning [1][2] Group 1: Medicare and Health Coverage - The six-month Medigap open enrollment period begins when enrolling in Medicare Part B, during which insurers cannot deny coverage or charge higher premiums, making it essential for retirees to act promptly [3] - Missing the Medigap enrollment window can lead to increased costs, limited options, or denials of coverage [3] Group 2: Financial Planning and Tax Implications - Converting pre-tax retirement accounts to a Roth IRA can have tax benefits, but large conversions may trigger IRMAA, increasing Medicare premiums based on income from two years prior [4] - Lump-sum payouts from unused vacation or sick time can elevate income above IRMAA thresholds, resulting in higher Medicare costs; spreading payouts across tax years may mitigate this [6] Group 3: Dental and Surgical Considerations - Medicare does not typically cover dental work, and standalone dental plans may have waiting periods, making it financially advantageous to complete major dental work before leaving employer coverage [5] - Planned surgeries, such as joint replacements, should ideally be handled before retirement to avoid significant out-of-pocket expenses [5]