If you predecease your wife or if she predeceases you, you/she will receive a step-up in basis on some/all of your investments, meaning that their appreciation will be calculated on the date of death. If you live in a community-property state (Arizona, California, Idaho, Louisiana, New Mexico, Nevada, Texas, Washington and Wisconsin) you receive a step-up in basis on both of your respective portions.You are, to employ a cliche, a victim of your own retirement success. You have invested so prodigiously that ...

Core Insights - A significant portion of U.S. crypto investors are unaware of their tax obligations related to digital assets, with only 25% currently tax compliant according to IRS metrics [1][2] - The introduction of new reporting rules, including the issuance of 1099 forms by crypto exchanges, is expected to increase awareness of tax compliance among investors [2][3] Group 1: Awareness and Compliance - Most crypto investors do not realize they need to file taxes on their digital asset activities, indicating a major awareness issue [2] - The IRS will require brokers to issue 1099 forms starting next year, which is anticipated to raise compliance awareness from 25% to nearly 100% [3] Group 2: Tax Implications - Tax liabilities can arise from various activities, including capital gains from selling assets and taxable events from swapping cryptocurrencies [4] - For example, transferring Bitcoin to Ethereum is considered a taxable event, which complicates tax reporting for active investors [4] Group 3: Strategic Tax Management - Investors are encouraged to utilize software solutions to manage their tax liabilities effectively, especially given the potential volume of trades [5] - Tax strategies such as tax-loss harvesting can provide advantages for frequent traders, allowing for more informed trading decisions [6]

Core Points - The One Big Beautiful Bill Act introduces significant tax changes for Americans, with many provisions effective in 2026 and some in 2025, prompting financial experts to advise proactive measures to enhance financial positions [1] Group 1: Charitable Giving - Taxpayers who itemize will lose deductions on the first 0.5% of their adjusted gross income (AGI) given to charity starting in 2026, which is a critical change [2] - For example, with an AGI of $100,000, the first $500 donated will not be deductible, and at $200,000 AGI, the first $1,000 will not provide any tax benefit [2] - Financial advisors recommend bundling multiple years of charitable donations into 2025 through a donor-advised fund (DAF) to maximize deductions and avoid capital gains taxes on appreciated securities [3] - Non-itemizers will receive a new above-the-line deduction of $1,000 for individuals and $2,000 for married couples filing jointly, applicable only to public charities [4] Group 2: Tax-Loss Harvesting - The tax law did not change capital gains treatment, allowing tax-loss harvesting strategies to remain effective [5] - By selling losing investments by December 31, taxpayers can offset gains and up to $3,000 of ordinary income [5] - Investors must be cautious of the wash-sale rule, which disallows losses if substantially identical stocks or securities are repurchased within 30 days before or after the sale [5]

Core Insights - The individual is considering withdrawing $30,000 from a Roth IRA for a home project to avoid capital gains taxes associated with a nonqualified brokerage account withdrawal [1][4] - The individual is 65 years old, in the 35% tax bracket, and not planning to retire soon, which influences the decision on which account to withdraw from [1][4] Tax Considerations - Withdrawing from the Roth IRA incurs no immediate tax implications since the individual is over 59 ½ years old [4] - Capital gains tax rates for the brokerage account withdrawal would be either 15% or 20%, depending on filing status and income [4] - It is important to consider long-term tax and financial planning implications when deciding on withdrawals from different accounts [2][3] Financial Strategy - If the individual is not close to the top of the 35% income tax bracket, using the brokerage account for withdrawal may be more beneficial while income supports the current tax bill [7] - Tax-loss harvesting opportunities should be reviewed within the brokerage account to offset capital gains and reduce tax liabilities [7][8] - The assumption that tax rates will be lower in retirement may not hold true, as current rates are set to expire at the end of 2025 [5]

Group 1 - The article discusses the increasing use of AI tools, particularly ChatGPT, for financial advice, with approximately half of Americans utilizing AI for personal finance management [1] - ChatGPT provides legal strategies for Americans to minimize their tax liabilities, emphasizing the importance of retirement and healthcare savings [2] - The AI suggests maximizing contributions to retirement accounts, such as 401(k) plans and traditional IRAs, with the 2025 contribution limits being $23,500 for 401(k) and $8,000 for traditional IRAs [2] Group 2 - ChatGPT highlights the benefits of Health Savings Accounts (HSAs), noting their triple tax advantage: contributions are tax-deductible, growth is tax-free, and withdrawals for qualified health expenses are not taxed [3] - The AI emphasizes the importance of tax credits, which can significantly reduce tax bills, mentioning specific credits like the child tax credit, earned income tax credit (EITC), and the American Opportunity Credit for college expenses [4] - Tax-loss harvesting is presented as a strategy to reduce taxable gains, allowing investors to offset capital gains with losses, up to a maximum of $3,000 of ordinary income [5]