Core Insights - The article discusses various strategies for managing capital gains taxes during retirement, particularly for individuals with significant investment portfolios and assets [2][4][10]. Tax Implications and Strategies - A step-up in basis allows heirs to inherit assets without the tax burden of capital gains accrued during the original owner's lifetime, applicable in community-property states [1][6]. - The long-term capital gains cap for 2025 is set at $533,401 for single filers and $600,051 for married couples filing jointly, with a net investment income tax applicable for incomes exceeding $250,000 for married couples [3][11]. - Tax-loss harvesting is recommended as a strategy to offset gains by selling stocks with unrealized losses [6]. Gifting and Charitable Contributions - Donating appreciated stock to charity can eliminate capital gains taxes and provide a tax deduction, with suggestions to pre-fund charitable giving through donor advised funds [7]. - Gifting appreciated stock to a family member in a lower tax bracket can shift the tax burden, with an annual gift-tax exclusion of $38,000 for married couples [8]. Financial Planning for Education - Establishing 529 accounts for grandchildren can help fund education and allows for tax benefits, including the application of the annual gift exclusion [9]. Retirement Financial Management - The article emphasizes the importance of consulting financial advisers for significant withdrawals and considering partial Roth conversions to optimize tax brackets [11][12]. - It highlights the financial security of being debt-free and having sufficient investments to enjoy retirement while planning for a financial legacy [10][12].