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Roth IRA Conversions: The Wisconsin Tax Law That Changes Everything – 11/29/2025

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John Berkley discusses a strong week for the markets, with the NASDAQ and Russell 2000 up about 5%, and the S&P 500 advancing 3.73%. The main focus, however, was the major change to retirement planning caused by a new Wisconsin state tax law. This law exempts up to $24,000 per person (age 67 or older) in retirement distributions (from sources like pensions, 401ks, and IRAs) from state tax.
This exemption significantly complicates Roth IRA conversions and 401k contributions, as paying conversion taxes now means potentially forfeiting future state tax-free distributions. The hosts emphasized that this “will change everything” regarding these decisions. Other topics included year-end tax loss selling (up to $3,000 against ordinary income), the growing complexity of tax and investment decisions, and estate planning issues, such as the tax implications of gifting assets (gifting basis) versus inheriting assets (stepped-up basis). The episode stressed the importance of continuity of income and relying on a financial advisor to navigate these intricate rules.

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