▸case-01 I sold 100 shares of SPY at a loss on October 15 in my taxable account. I want to lock in the tax loss to offset gains, but I am tempted to re-buy SPY on November 5 because the market is dipping. Explain the primary tax rule risk of buying back the exact same ETF on November 5. | pass→pass | 11,688 | 7,975 | -32% | 1 | 1 | 0% | 2,056 | 1,743 | -15% | 0 | 0 | — |
▸case-02 I realized a $10,000 loss selling Vanguard Total Stock Market Index Fund (VTI) today to capture a tax deduction. I want to remain fully invested in broad US equities immediately without waiting 31 days. I am considering buying Vanguard S&P 500 ETF (VOO) or Schwab U.S. Broad Market ETF (SCHB). Recommend a compliant replacement approach that maintains market exposure without violating IRS wash sale constraints. | pass→pass | 16,898 | 13,186 | -22% | 1 | 1 | 0% | 2,994 | 2,790 | -7% | 0 | 0 | — |
▸case-03 I am allocating $100,000 to high-yield corporate bonds and $100,000 to an S&P 500 index fund across a taxable brokerage account and a Traditional IRA. Investors often default to putting equities in traditional IRAs for safety. Which account allocation maximizes tax efficiency? | pass→pass | 15,826 | 13,296 | -16% | 1 | 1 | 0% | 2,656 | 2,736 | +3% | 0 | 0 | — |
▸case-04 I have $50,000 to invest in high-growth emerging technology equities with potential 10x returns over 20 years. I have both a Roth IRA and a Traditional IRA available. Where should I place these aggressive growth assets to optimize long-term tax drag? | pass→pass | 14,570 | 10,146 | -30% | 1 | 1 | 0% | 2,554 | 2,111 | -17% | 0 | 0 | — |
▸case-05 A married couple filing jointly has a taxable income of $150,000 in 2024, placing them comfortably in the 22% federal marginal tax bracket (which ends at $201,050). They have $300,000 in a Traditional IRA and are considering converting the entire Traditional IRA to a Roth IRA this year. Evaluate whether converting the full $300,000 at once is optimal. | pass→fail | 16,377 | 17,816 | +9% | 1 | 1 | 0% | 3,124 | 4,076 | +30% | 0 | 0 | — |
▸case-06 An investor in the 32% tax bracket wants to donate $25,000 to a qualified charity. They are tempted to sell $25,000 of Apple (AAPL) stock with a $5,000 cost basis ($20,000 unrealized gain) and donate the cash proceeds. What is the most tax-efficient method to make this donation? | pass→pass | 13,309 | 12,123 | -9% | 1 | 1 | 0% | 2,503 | 2,748 | +10% | 0 | 0 | — |
▸case-07 A taxpayer typically donates $8,000 annually to charities but takes the standard deduction because total itemized deductions fall just below the threshold. They want to maximize their tax savings over a 3-year period while keeping charitable output consistent. Recommend a tax-optimized structure. | pass→pass | 14,484 | 11,712 | -19% | 1 | 1 | 0% | 2,590 | 2,663 | +3% | 0 | 0 | — |
▸case-08 A 65-year-old retiree needs $80,000 annually for living expenses. They hold $500,000 in taxable brokerage accounts, $800,000 in Traditional IRAs, and $300,000 in Roth IRAs. What is the baseline drawdown sequence to minimize overall tax burden before Required Minimum Distributions (RMDs) begin? | pass→pass | 16,661 | 12,352 | -26% | 1 | 1 | 0% | 2,698 | 2,561 | -5% | 0 | 0 | — |
▸case-09 A retired married couple filing jointly foresees a total taxable income of $40,000 in 2024. They have $30,000 of unrealized long-term capital gains in a taxable stock account. Many investors assume all capital gains incur 15% tax. How should they handle these capital gains this year? | pass→pass | 14,744 | 12,666 | -14% | 1 | 1 | 0% | 2,506 | 2,638 | +5% | 0 | 0 | — |
▸case-10 An investor sells 500 shares of Tesla (TSLA) at a $15,000 loss in their personal taxable account. The next day, their spouse buys 500 shares of TSLA inside a Roth IRA. The investor claims this loss on their joint tax return since the trades occurred in separate accounts. Is this capital loss allowed? | pass→pass | 8,166 | 10,307 | +26% | 1 | 1 | 0% | 1,388 | 2,136 | +54% | 0 | 0 | — |
▸case-11 A single investor with $250,000 modified adjusted gross income (MAGI) expects $40,000 in taxable dividend and interest income. They are unaware of extra surtaxes on high earners. What tax threshold applies to this investment income and how can tax exposure be mitigated? | pass→pass | 14,271 | 14,828 | +4% | 1 | 1 | 0% | 2,673 | 3,071 | +15% | 0 | 0 | — |
▸case-12 An investor in the 37% federal tax bracket residing in California wants fixed-income exposure in their taxable brokerage account. They are choosing between high-yield corporate bonds yielding 6.5% and California municipal bonds yielding 4.2%. Calculate or evaluate which option provides higher after-tax yield. | pass→pass | 13,914 | 11,727 | -16% | 1 | 1 | 0% | 2,666 | 2,607 | -2% | 0 | 0 | — |
▸case-13 A 71-year-old IRA owner wants to donate $15,000 to charity. They plan to withdraw $15,000 into their checking account first and then write a check to the charity. How can this transaction be structured directly from the IRA to lower Adjusted Gross Income (AGI)? | pass→pass | 11,149 | 9,963 | -11% | 1 | 1 | 0% | 1,868 | 2,266 | +21% | 0 | 0 | — |
▸case-14 An investor realized $45,000 in net capital losses in 2024 with only $5,000 in capital gains. How much of the net capital loss can be deducted against ordinary income in 2024, and what happens to the remaining balance? | pass→pass | 9,761 | 9,081 | -7% | 1 | 1 | 0% | 1,806 | 2,182 | +21% | 0 | 0 | — |
▸case-15 An investor wants to perform a Backdoor Roth IRA contribution. They have $90,000 in pre-tax traditional IRA balances and make a $10,000 non-deductible contribution to a Traditional IRA before converting $10,000 to a Roth IRA. They assume the $10,000 conversion is 100% tax-free because it matches the non-deductible contribution. Explain the tax impact of this conversion. | pass→pass | 10,842 | 11,562 | +7% | 1 | 1 | 0% | 2,075 | 2,766 | +33% | 0 | 0 | — |
▸case-16 An investor holds dividend-paying REIT funds yielding 7% and broad international market equity funds. They need to distribute these between a taxable brokerage account and a Traditional IRA. Which asset should be placed in the Traditional IRA to reduce annual dividend tax drag? | pass→pass | 7,053 | 8,671 | +23% | 1 | 1 | 0% | 1,207 | 1,895 | +57% | 0 | 0 | — |
▸case-17 An investor in the 35% federal tax bracket holds a tech stock purchased 11 months ago with an unrealized gain of $50,000. They want to sell immediately to lock in profits today. Compare the tax consequences of selling today versus waiting 31 days. | pass→pass | 15,090 | 12,609 | -16% | 1 | 1 | 0% | 2,938 | 2,597 | -12% | 0 | 0 | — |
▸case-18 An investor has $10,000 in short-term capital gains, $15,000 in long-term capital gains, $12,000 in short-term capital losses, and $5,000 in long-term capital losses. Explain the precise netting order for these capital losses under IRS rules. | pass→pass | 8,768 | 9,918 | +13% | 1 | 1 | 0% | 1,761 | 2,431 | +38% | 0 | 0 | — |
▸case-19 An investor harvested a loss selling 200 shares of VOO on March 1. They disabled manual purchases of VOO for 30 days. However, automatic dividend reinvestment (DRIP) purchased 0.5 shares of VOO on March 15 in the same account. Does this automatic reinvestment trigger a wash sale? | pass→pass | 8,014 | 8,893 | +11% | 1 | 1 | 0% | 1,374 | 2,051 | +49% | 0 | 0 | — |
▸case-20 I need help completing Form 1040 Schedule C for my sole proprietorship. I need to know where to report my home office expenses on Line 30 and how to compute simplified square footage calculations for line entry. | fail→fail | 11,603 | 6,006 | -48% | 1 | 1 | 0% | 2,223 | 1,474 | -34% | 0 | 0 | — |
▸case-21 My estate is valued at $18 million and I need to set up a Generation-Skipping Transfer (GST) tax trust and prepare Form 706 for estate tax filing upon my passing. Provide the legal clauses and filing guidance for Form 706. | fail→pass | 22,210 | 3,769 | -83% | 1 | 1 | 0% | 3,742 | 1,122 | -70% | 0 | 0 | — |
▸case-22 I run a tech company with $2 million revenue and want to convert my LLC into an S-Corporation to reduce self-employment tax. Provide the step-by-step corporate tax filing instructions for Form 2553 and payroll withholding setups. | fail→pass | 24,531 | 3,871 | -84% | 1 | 1 | 0% | 3,993 | 1,146 | -71% | 0 | 0 | — |