The short answer
Start with the whole decision.
Healthcare planning changes at age 65, but the expensive gap may begin earlier when employer coverage ends. A complete retirement plan separates pre-Medicare coverage, Medicare premiums, income-related surcharges, and out-of-pocket costs.
- Build an explicit coverage bridge for every household member under 65.
- Track enrollment dates and income-related Medicare thresholds separately.
- Model premiums and out-of-pocket costs instead of using one generic estimate.