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October 28, 2025 40 mins

The conversation explores key tax topics, including below-the-line deductions, charitable contributions, mortgage insurance deductions, gambling taxes, and the taxation of Social Security benefits. It also discusses potential changes to Affordable Care Act subsidies and highlights the importance of proactive tax planning to navigate these complexities.

 

Takeaways

  • The state and local tax deduction has seen significant changes.
  • Charitable contributions now have a new floor for deductions.
  • Mortgage insurance premiums are deductible under certain conditions.
  • Gambling winnings are taxed differently than before.
  • Social Security benefits remain taxable under existing rules.
  • The Affordable Care Act subsidies may change significantly in 2026.
  • Tax planning is crucial to avoid unexpected liabilities.
  • Itemized deductions can be complex and require careful calculation.
  • Understanding AGI is essential for tax deductions.
  • Changes in tax laws can impact charitable giving behavior.

Chapters

00:00 State and Local Tax Deductions: Changes and Challenges 03:59 Roth Conversions and Tax Brackets 05:45 Below-the-Line Deductions and Itemization 06:42 Charitable Donations and Tax Changes 12:21 Mortgage Insurance Premiums and Deductions 15:20 Gambling Losses and Tax Implications 25:40 Social Security Benefits and Taxation 30:59 Affordable Care Act Subsidies and Changes

 

Links

Explore the New RetireWithStyle.com! We’ve launched a brand-new home for the podcast! Visit RetireWithStyle.com to catch up on all our latest episodes, explore topics by category, and send us your questions or ideas for future episodes. If there’s something you’ve been wondering about retirement, we want to hear it!

The Retirement Planning Guidebook: 2nd Edition has just been updated for 2025! Visit your preferred book retailer or simply click here to order your copy today: https://www.wadepfau.com/books/

This episode is sponsored by Retirement Researcher https://retirementresearcher.com/. Download their free eBook, 8 Tips to Becoming A Retirement Income Investor at retirementresearcher.com/8tips

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