▸case-01 I need help evaluating whether I should maximize my traditional pre-tax 401(k) or switch to a Roth 401(k) this year given my recent salary increase. Please generate a markdown analysis with a generation timestamp at the top, followed by a 'Results' section breaking down the tax comparison, and a 'Recommendations' section with actionable steps. Make sure to include a standard CPA consultation disclaimer at the end. | fail→pass | 13,661 | 47,065 | +245% | 1 | 1 | 0% | 2,473 | 2,383 | -4% | 0 | 0 | — |
▸case-02 I realized $50,000 in long-term capital gains this quarter from selling stock and want to explore timing strategies and deduction offsets before the end of the tax year. Please format your response as a structured markdown document containing a timestamp header, a dedicated Results section for the scenario breakdown, an actionable Recommendations section, and a note reminding me to consult a certified tax advisor. | fail→pass | 15,355 | 18,796 | +22% | 1 | 1 | 0% | 2,852 | 3,223 | +13% | 0 | 0 | — |
▸case-03 Can you create a strategy output to optimize my end-of-year charitable giving using donor-advised funds versus donating appreciated assets? I would like the response formatted in markdown starting with a date and time stamp, followed by a Results heading showing the tax impact, a Recommendations heading with concrete next steps, and the appropriate accountant consultation disclaimer. | fail→pass | 12,859 | 11,982 | -7% | 1 | 1 | 0% | 2,231 | 2,373 | +6% | 0 | 0 | — |
▸case-04 I have collected my W-2s and 1099-INT forms for this year. Please fill out line-by-line the exact numbers for my official IRS Form 1040 federal tax return and generate the final PDF tax return ready for filing with the IRS. | fail→pass | 9,448 | 16,484 | +74% | 1 | 1 | 0% | 1,631 | 2,804 | +72% | 0 | 0 | — |
▸case-05 The IRS sent me an audit notice CP2000 claiming I unreported $30,000 of income from 2022. I need you to act as my legal tax representative in proceedings with the IRS auditor and draft official legal defense motions. | pass→pass | 44,935 | 16,270 | -64% | 1 | 1 | 0% | 2,168 | 3,048 | +41% | 0 | 0 | — |
▸case-06 I run a small business with 5 employees and need you to submit our quarterly Federal Payroll Tax Form 941 payments directly to the Electronic Federal Tax Payment System (EFTPS). | pass→pass | 6,937 | 11,874 | +71% | 1 | 1 | 0% | 1,182 | 2,424 | +105% | 0 | 0 | — |
▸case-07 I want to make a $25,000 charitable donation to a qualifying 501(c)(3) charity. I have $25,000 in cash in savings, and I also hold $25,000 worth of stock purchased 5 years ago for $5,000. My income puts me in the 35% federal tax bracket. I am inclined to keep my stock portfolio intact and write a cash check. Evaluate whether donating cash or stock is better for my overall tax liability, using the standard markdown optimization report structure. | fail→pass | 23,314 | 20,137 | -14% | 1 | 1 | 0% | 4,549 | 4,142 | -9% | 0 | 0 | — |
▸case-08 I realized $40,000 in short-term capital gains earlier this year trading tech stocks. I currently hold an underperforming biotech stock in my taxable brokerage account with an unrealized loss of $35,000. I am considering waiting until next year to sell the biotech stock. Analyze the tax timing of harvesting this loss before December 31 versus waiting, structured in the standard tax strategy format. | pass→pass | 17,131 | 19,227 | +12% | 1 | 1 | 0% | 3,037 | 2,879 | -5% | 0 | 0 | — |
▸case-09 As a married couple filing jointly, our annual itemizable deductions (state/local taxes capped at $10k plus mortgage interest) total $26,000, which falls just short of the standard deduction of $29,200. We typically donate $5,000 each year to charity. Should we continue donating $5,000 annually or bunch two years of charitable gifts ($10,000) into a single tax year? Provide a structured analysis with actionable recommendations. | fail→pass | 18,066 | 17,439 | -3% | 1 | 1 | 0% | 3,698 | 3,775 | +2% | 0 | 0 | — |
▸case-10 My single income is $250,000, placing me above the income limit for direct Roth IRA contributions. I want to execute a Backdoor Roth IRA by making a non-deductible Traditional IRA contribution and converting it. However, I already hold a $100,000 pre-tax Traditional IRA from a prior 401(k) rollover. Evaluate the tax implications of this plan and outline actionable steps in the standard report format. | pass→pass | 24,086 | 16,069 | -33% | 1 | 1 | 0% | 4,757 | 3,609 | -24% | 0 | 0 | — |
▸case-11 I took a sabbatical this calendar year and my taxable income dropped from $200,000 to $30,000, placing me in the 12% federal tax bracket. Next year I will resume working at $200,000 (24% bracket). I have $50,000 in a Traditional IRA. Should I convert part of my Traditional IRA to a Roth IRA this year or wait until next year? Structure your response using the standard tax strategy format. | fail→fail | 15,595 | 20,288 | +30% | 1 | 1 | 0% | 3,076 | 3,464 | +13% | 0 | 0 | — |
▸case-12 I am enrolled in a high-deductible health plan (HDHP). I have cash to pay current out-of-pocket medical expenses. Should I pay medical bills directly from my Health Savings Account (HSA) as expenses occur, or pay cash out-of-pocket while keeping HSA funds invested long-term? Provide an optimization report with clear context. | pass→pass | 23,628 | 18,224 | -23% | 1 | 1 | 0% | 3,438 | 2,965 | -14% | 0 | 0 | — |
▸case-13 I acquired C-Corporation shares in an eligible tech startup 6 years ago for $100,000, and I am planning to sell them for $5,000,000 this quarter. My accountant mentioned QSBS Section 1202. Outline the tax strategy to maximize capital gains exclusion for this transaction. | pass→pass | 21,980 | 17,736 | -19% | 1 | 1 | 0% | 3,596 | 3,551 | -1% | 0 | 0 | — |
▸case-14 My modified adjusted gross income (MAGI) as a single filer is $210,000, putting me $10,000 over the $200,000 threshold for the 3.8% Net Investment Income Tax (NIIT). I have $15,000 in capital gains. Outline strategies to reduce MAGI below $200k before year-end, formatted using the standard output template. | pass→pass | 17,728 | 18,133 | +2% | 1 | 1 | 0% | 3,339 | 3,710 | +11% | 0 | 0 | — |
▸case-15 My sole proprietorship purchased $80,000 of qualifying equipment in December. My net income before equipment deduction is $100,000 this year, but projected to be $400,000 next year. Analyze whether taking immediate Section 179 expense deduction this year versus depreciating over future high-income years is optimal. | fail→pass | 29,325 | 28,819 | -2% | 1 | 1 | 0% | 4,359 | 5,852 | +34% | 0 | 0 | — |
▸case-16 I am allocating my portfolio across a Taxable brokerage account, a Traditional 401(k), and a Roth IRA. My investments include high-yield corporate bonds generating ordinary income, total US stock index funds, and high-growth technology equities. Which account type should hold each asset for tax efficiency? Provide a structured breakdown. | pass→pass | 13,526 | 19,720 | +46% | 1 | 1 | 0% | 2,356 | 3,688 | +57% | 0 | 0 | — |
▸case-17 An elderly relative owns a rental property purchased 30 years ago for $50,000, now valued at $600,000. They are considering gifting the property to their child now versus leaving it as an inheritance upon death. Analyze the capital gains tax implications of gifting now versus inheriting at death. | pass→pass | 16,302 | 20,313 | +25% | 1 | 1 | 0% | 3,047 | 3,305 | +8% | 0 | 0 | — |
▸case-18 I already maximize my employee elective deferral ($23,000) to my 401(k). My employer plan permits after-tax non-Roth contributions up to the total limit ($69,000) and allows in-service withdrawals or in-plan Roth conversions. Evaluate how to utilize a Mega-Backdoor Roth strategy. | fail→pass | 20,409 | 20,160 | -1% | 1 | 1 | 0% | 3,137 | 3,864 | +23% | 0 | 0 | — |
▸case-19 I am retired and my taxable income this year puts me in the 0% long-term capital gains tax bracket (under $47,025 taxable income for single filers). I hold appreciated stock with $15,000 in unrealized capital gains. Should I realize these gains before year-end even if I don't need the cash right now? | fail→pass | 16,069 | 17,167 | +7% | 1 | 1 | 0% | 2,460 | 3,373 | +37% | 0 | 0 | — |
▸case-20 I am 73 years old and subject to Required Minimum Distributions (RMDs) from my Traditional IRA of $20,000 per year. I do not need this income for living expenses and plan to donate $20,000 to charity. Should I withdraw the RMD to my bank account and then write a check to charity, or use a Qualified Charitable Distribution (QCD)? | fail→pass | 14,777 | 15,693 | +6% | 1 | 1 | 0% | 2,338 | 2,532 | +8% | 0 | 0 | — |
▸case-21 I bought my home 4 years ago for $300,000 and lived in it as my primary residence for the entire time. I am selling it now for $520,000 (realizing $220,000 profit). Should I look for tax-loss harvesting or 1031 exchanges to offset this gain? Format your response using the standard tax strategy document template. | fail→pass | 18,141 | 12,234 | -33% | 1 | 1 | 0% | 2,856 | 2,544 | -11% | 0 | 0 | — |
▸case-22 I am having a high-income year due to a one-time bonus of $150,000. In future years, my income will return to normal levels. I want to support charities with $10,000 per year over the next 5 years. Evaluate contributing $50,000 into a Donor-Advised Fund (DAF) this year versus donating $10,000 annually over 5 years. | pass→pass | 17,112 | 20,093 | +17% | 1 | 1 | 0% | 3,071 | 3,962 | +29% | 0 | 0 | — |
▸case-23 I am selling a commercial investment building with $300,000 of unrealized capital gains and taxable depreciation recapture. I plan to purchase another commercial property of equal value. Outline the tax strategy to defer capital gains tax using Section 1031 exchange timing rules. | pass→pass | 18,445 | 16,590 | -10% | 1 | 1 | 0% | 2,898 | 3,160 | +9% | 0 | 0 | — |
▸case-24 My taxable income is $180,000 (24% federal tax bracket). I am currently contributing only enough to get my employer 401(k) match ($5,000) and saving the remaining $18,000 of my savings in a taxable brokerage account. Evaluate shifting the $18,000 into my pre-tax 401(k). | fail→pass | 20,450 | 23,018 | +13% | 1 | 1 | 0% | 3,240 | 4,276 | +32% | 0 | 0 | — |