Find a CPA Who Understands Your Situation
In-depth guides on tax situations, sourced from IRS publications and tax code, with a free matching tool to find your specialist.
Not Sure What Type of Tax Professional You Need?
Answer a few questions about your situation and get a personalized recommendation for CPA specializations, interview questions, and a comparison worksheet.
Step-Up in Basis: The Most Valuable Tax Concept Most People Have Never Heard Of
When you inherit an asset, the IRS resets its taxable "purchase price" to whatever it was worth on the day the previous owner died. This can eliminate decades of accumulated capital gains in a single event, potentially saving heirs tens or even hundreds of thousands of dollars.
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Tax rules vary significantly by state. Your location helps us recommend the right specializations and build a local search.
The timing affects filing status, deadlines for step-up documentation, and which tax strategies are still available.
Different assets have different tax rules. Real estate and investments may have unrealized gains eligible for step-up basis.
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The entity type determines how step-up in basis works, which elections are available (Section 754, 338(h)(10)), and whether S-corp eligibility could be at risk.
Whether you keep, sell, or wind down the business determines which tax strategies are most important and how urgently you need certain expertise.
Revenue indicates the complexity of the engagement and helps match you with a CPA who handles businesses of similar size.
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Asset purchases let you step up basis and accelerate depreciation. Stock purchases inherit the company's existing basis and potential liabilities. This single decision can mean hundreds of thousands in tax differences.
Deals closing within 30 days have very little planning window. Engaging a CPA early gives you the best chance to structure the deal favorably before terms are locked in.
Financing structure affects interest deductibility (Section 163(j) limits), entity choice, and documentation requirements. SBA loans have specific CPA documentation needs.
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Entity type determines whether you face double taxation (C-corp asset sale), qualify for QSBS exclusion (C-corp stock), or can use pass-through treatment. This is the most fundamental factor in sale planning.
More lead time means more planning options. With 1-2 years, you can verify QSBS eligibility, change state residency, or restructure the entity. Under 3 months, the focus shifts to execution.
Ownership over 5 years in a C-corp may qualify for the Section 1202 QSBS exclusion, which can eliminate federal tax on up to $10 million in gains. This is often the single largest tax-saving opportunity.
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Portfolio size determines whether cost segregation, entity restructuring, and advanced passive loss strategies are worth pursuing. Larger portfolios require a CPA who specializes in real estate investors.
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1031 exchanges defer capital gains tax but have strict 45-day identification and 180-day closing deadlines with no extensions. Your CPA should have hands-on exchange experience and relationships with qualified intermediaries.
Real Estate Professional Status (REPS) allows rental losses to offset W-2 and other income, potentially saving thousands in taxes. It requires 750+ hours and more than half your working time in real property activities. The IRS heavily audits REPS claims.
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ISOs, NSOs, RSUs, and ESPPs each have fundamentally different tax treatment. The planning strategies depend entirely on which types you hold.
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Pre-IPO equity has liquidity constraints, valuation complexity, and potential QSBS eligibility. Public company equity allows immediate sale but may involve insider trading rules.
Prior exercises affect your AMT credit carryforward, holding period tracking, and whether you may have disqualifying disposition risk.
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Different professions have different tax characteristics. Doctors, lawyers, and consultants are classified as Specified Service Trades or Businesses, which affects the QBI deduction and other planning strategies.
W-2, 1099, and K-1 income each have different tax characteristics. 1099 income creates self-employment tax exposure but also opens entity structure and retirement plan opportunities.
Retirement plan optimization is often the single biggest tax savings opportunity for high earners. The wrong plan can leave $30K-$200K per year on the table.
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Whether you are planning to move, currently abroad, or returning to the US determines which tax rules apply and what planning needs to happen now.
Longer periods abroad create more accumulated compliance complexity, affect bona fide residence qualification, and increase the likelihood of unreported foreign accounts or investments.
Foreign accounts trigger FBAR reporting (accounts over $10,000 aggregate) and FATCA compliance (Form 8938). Non-willful FBAR penalties can reach $12,500 per violation; willful violations can exceed $100,000 per account per year.
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Different business types have different deduction opportunities, audit risk profiles, and tax planning strategies. A CPA with industry experience can help you maximize deductions specific to your business.
Revenue level determines whether entity restructuring (like S-corp election) makes sense, what retirement plan options are most valuable, and the level of tax planning complexity needed.
Missing quarterly estimated payments triggers underpayment penalties (currently ~8% annualized). Many first-time business owners don't know they need to make them.
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Your Personalized CPA Guide
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Questions to Ask in Your Consultations
Tailored based on your situation. Use these to evaluate which CPA is the right fit.
Quick Guides for Your Situation
Based on your answers, these guides explain the tax concepts most relevant to you.
CPA Comparison Worksheet
Print this worksheet and fill it in during or after your consultations. Comparing CPAs side-by-side makes the decision clearer.
| Factor | CPA 1 | CPA 2 | CPA 3 |
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| Understood my situation | |||
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| Proactive planning approach | |||
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| Fee structure clear | |||
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| Overall fit (1-5) | |||
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