Category: Tax Policy
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The IRS is bloated and ineffective, and progressives have it backwards
Progressives push for a bigger IRS, but the agency’s real problems are structural and self-inflicted. Here’s why more funding hasn’t fixed enforcement gaps.
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Not all loopholes are unfair
The word loophole gets used as an automatic accusation. Some are real abuses, but many are deliberate policy choices working as designed. Telling them apart matters.
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Most CPAs aren’t worth what they charge
A good CPA earns their fee many times over. A mediocre one charges premium rates for work software handles. Knowing the difference saves real money.
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Free File is sabotaged on purpose and nobody goes to jail
The IRS Free File program exists. Most eligible taxpayers never see it because the major tax prep companies have spent two decades hiding it on purpose.
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529 plans are a tax break for parents who didn’t need help
529 plans deliver real tax savings, but the families using them are mostly wealthy. The policy is regressive by design and rarely scrutinized that way.
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Wealth taxes do work and the data is clear
Wealth taxes are dismissed as unworkable, but recent research and updated implementations show they raise revenue and don’t trigger the exodus critics predict.
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Harvard’s endowment should be taxed like a corporation
Harvard’s $50 billion endowment operates like a hedge fund with a school attached. The current 1.4% excise tax is a token. Here’s the case for treating it as what it is.
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The step-up in basis is the single biggest wealth-transfer loophole and untouchable
The step-up in basis erases trillions in capital gains tax at death. Every reformer eyes it; none touch it. Here’s why it survives every administration.
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The American tax system is a wealth-preservation engine
Wages get taxed at full rates while capital, inheritance, and asset appreciation get every break in the code. The system isn’t broken — it’s working as designed.
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HSAs are a tax shelter for the rich
Health Savings Accounts are sold as healthcare reform, but the tax advantages disproportionately benefit high earners who can afford to leave the money invested for decades.