Naples is wealthier and older than almost anywhere in the country, but two groups show up again and again in consultations, and each has a distinctly Florida version of the same planning question.
Affluent Retirees & Snowbirds
Many Naples residents are retired or semi-retired, often arriving from higher-tax states in the Midwest and Northeast with substantial savings and a home up north. The appeal is real, no state income tax and strong homestead protection, but with larger balances the long-term care bill, the IRMAA cliffs, and the estate details are what catch people off guard, especially under Florida's common-law and homestead rules.
- ✓ The Roth-conversion window between retirement and RMDs (age 73), sized to a larger portfolio
- ✓ IRMAA cliffs at $109K single or $218K joint MAGI (2026), which higher incomes hit more often
- ✓ Long-term care to protect substantial assets, often paired with the Florida Partnership and homestead protection
- ✓ Residency and domicile questions for part-year residents who own property in two states
Business Owners & High-Net-Worth Families
Naples is full of family businesses, retired executives, and professionals whose wealth is tied up in a company, real estate, or a concentrated portfolio. For them the questions move past income replacement toward keeping a business in the family, equalizing an inheritance fairly, and making sure beneficiaries, trusts, and the homestead all point the same direction.
- ✓ Buy-sell agreements and key-person coverage for closely held businesses
- ✓ Life insurance for estate liquidity and inheritance equalization, not just income
- ✓ Beneficiaries coordinated with Florida's elective share, homestead-descent rules, and any trust
- ✓ Own-occupation disability coverage for still-working professionals and owners