Tag: tax
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The Curious Case of OBBBA Tax Savings
The 2025 One Big Beautiful Bill Act (OBBBA) reform was intended to make one of the biggest changes to Social Security taxation in decades. Most commentary focuses on the headline feature – eliminating the taxation of Social Security benefits for the majority of retirees – but the real story sits deeper in the details. OBBBA…
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Tax Gain Harvesting: Extreme Caution at Long Horizons
Many investors have heard of tax-loss harvesting, but its lesser-known cousin – tax gain harvesting (TGH) – is often misunderstood. While it might sound appealing to sell appreciated assets to reset your cost basis, the reality is that: over long investment horizons, harvesting gains can actually reduce your after-tax wealth unless your current tax rate…
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How Roth Conversions Affect ACA and IRMAA Subsidies
When planning a Roth conversion, it’s easy to focus only on the income tax impact. But if you’re on ACA health insurance or Medicare, the conversion can also trigger changes in your ACA subsidies and IRMAA surcharges. In this example, we’ll quantify: Problem Setup We compare two scenarios: Our goal is to measure how much…
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A Guide to U.S. Income Categories for Tax Planning
When it comes to tax planning, not all income is created equal.Two people could both “earn” $100K a year and still end up paying very different amounts in federal and state taxes – simply because of what type of income it is. At Princeton Asset, we think the first step to building a bulletproof tax…