Personal Tax Preparation for Complex Financial Situations
Rental income, investment portfolios, sole proprietorships, multi-state filing, cryptocurrency — when your tax situation is more than a W-2 and a simple return, we handle all of it correctly.
Who this is built for
- Rental property owners (long-term & Airbnb)
- Stock, bond & mutual fund investors
- Cryptocurrency traders & holders
- Freelancers, contractors & sole proprietors
- Multi-state residents or workers
- Small business owners (pass-through K-1s)
- Life events: marriage, divorce, home sale
Personal Tax for Situations That Require Real Expertise
Standard tax software struggles with complexity. When your return involves multiple income types, multiple states, or intricate deduction calculations, you need someone who knows the rules.
Rental Property Owners
Long-term and short-term (Airbnb) rental income, depreciation, passive activity rules, and 1031 exchanges.
Investors & Traders
Stocks, ETFs, mutual funds, options, and cryptocurrency. Capital gains optimization and wash sale tracking.
Self-Employed & Freelancers
Schedule C reporting, SE tax, home office, vehicle deductions, and retirement contribution maximization.
Multi-State Filers
Worked in multiple states? Changed residency? We prepare all required state returns with correct income allocation.
Three Complex Schedules We Know Inside and Out
Schedule E, Schedule D, and Schedule C cover the most common complex tax situations. Here's exactly what we handle in each area.
Rental Income & Real Estate
Passive activity rules, depreciation, and property-level reporting
- Long-term rental income & expenses reported by property
- 27.5-year MACRS depreciation on residential rental properties
- Passive activity loss rules & the $25,000 passive loss allowance
- Short-term rental (Airbnb, VRBO) — material participation test
- Vacation home rules: personal-use days vs. rental days calculation
- 1031 Like-Kind Exchange deferral reporting
- Property sale — depreciation recapture (Section 1250) at 25%
- K-1 income from S-Corps, partnerships, and trusts (also Schedule E)
Capital Gains & Investments
Short-term and long-term rates, wash sales, and crypto reporting
- Short-term gains (held <1 year) taxed as ordinary income
- Long-term gains (held 1+ years) at 0%, 15%, or 20% preferential rates
- Wash sale rule — prohibited loss deferrals on repurchased securities
- Cryptocurrency — every transaction is a taxable event under IRS guidance
- Stock options — ISO vs. NSO treatment and AMT implications
- Mutual fund capital gain distributions from 1099-DIV
- Qualified small business stock (QSBS) exclusion — Section 1202
- Capital loss carryforward from prior years applied correctly
Self-Employment & Sole Proprietors
SE tax, home office, vehicle, and retirement deductions
- Self-employment tax (15.3% on net SE income) & deductible half
- Home office deduction — simplified ($5/sq ft, up to 300 sq ft) or actual
- Vehicle deduction — standard mileage ($0.67/mile for 2024) vs. actual costs
- Business meals (50% deductible), software, subscriptions, equipment
- Health insurance premium deduction for self-employed individuals
- SEP-IRA (up to 25% of net SE income or $66,000), SIMPLE IRA, Solo 401(k)
- Qualified Business Income (QBI) deduction — 20% of eligible net income
- Estimated quarterly payment planning to avoid underpayment penalties
Rental Property Tax Is More Complicated Than Most People Realize
Rental income is fully taxable, but the deductions available can dramatically reduce or even eliminate the taxable amount. The rules around passive activity losses, depreciation, and short-term rentals are some of the most commonly misapplied areas of the tax code.
We track your basis in each property, calculate depreciation correctly each year, apply the passive activity rules accurately, and ensure you're capturing every allowable deduction — without triggering the IRS issues that sloppy rental tax prep can cause.
Short-term rental exception: If you rent a property for fewer than 15 days per year, the income is excluded from gross income and the expenses are not deductible. This creates specific opportunities — and specific traps — for Airbnb-style rental situations.
- ✓Depreciation never takenMany rental owners don't take depreciation every year — and then face the IRS taxing the theoretical depreciation at sale regardless. We correct this and get you current.
- ✓Passive losses suspendedPassive activity losses in excess of passive income are suspended — not lost. We track them annually and release them at sale or against qualifying passive income.
- ✓Airbnb treated like a W-2Short-term rental income is often subject to different rules than long-term rental income. We apply the correct test and ensure the right schedule and treatment.
- ✓Mixed personal & rental useVacation homes with both personal and rental days require careful allocation of expenses. We apply the IRS formula correctly — not the common, incorrect approach.
Every Crypto Transaction Is a Tax Event — We Track All of Them
The IRS treats cryptocurrency as property. That means every sale, trade, or conversion is a taxable event that creates either a capital gain or loss. This includes trading crypto-to-crypto, using crypto to buy goods, and receiving crypto as payment for services.
We import your transaction history from all exchanges, apply the correct cost basis method (FIFO, LIFO, or specific identification), calculate gains and losses, and report them on Form 8949 and Schedule D — accurately.
Staking & DeFi income is treated as ordinary income in the year received (at fair market value at receipt), then as a capital gain or loss when later sold. We report both stages correctly.
Not Just Reporting — Optimizing
- ✓Tax-loss harvestingIdentifying investment losses to offset gains, reducing your net capital gain subject to tax — while respecting wash sale rules.
- ✓Holding period optimizationKnowing whether to hold a position another few weeks to qualify for long-term rates (15–20%) vs. short-term (ordinary income rates) can significantly affect your tax bill.
- ✓Net Investment Income TaxThe additional 3.8% NIIT on investment income above income thresholds ($200k single / $250k MFJ). We calculate, plan around, and report correctly.
- ✓Qualified dividends vs. ordinary dividendsQDI receives the same preferential rates as long-term gains. We apply the correct rate — not the ordinary income rate — to every qualifying dividend.
Lived in Two States? Worked Remotely Across State Lines?
Multi-state filing is required when you earned income in more than one state, changed your state of domicile during the year, own rental property in a state where you don't live, or work remotely for an employer in another state.
Each state has different residency rules, income sourcing rules, and credit provisions for taxes paid to other states. Filing incorrectly — or failing to file where required — can result in penalties, interest, and aggressive collection by state revenue departments.
We prepare all required state returns with correct income allocation and apply credits properly so you're not taxed twice on the same income.
Major Life Changes Create Major Tax Implications
- ✓Getting marriedFiling jointly vs. separately — the "marriage bonus" or "marriage penalty" depends on your combined income structure. We model both.
- ✓DivorceAlimony rules changed under TCJA. Asset division, QDRO retirement account splits, and dependency claims all have tax implications that must be handled correctly.
- ✓Home purchase or saleThe $250,000/$500,000 primary residence exclusion (Section 121), ownership and use tests, and depreciation recapture if the home was ever a rental.
- ✓Starting a businessFirst year as self-employed? SE tax, estimated payments, home office setup, and first-year deduction elections require careful first-return planning.
- ✓Inheritance or giftStepped-up basis on inherited assets. Gift tax exclusions ($18,000 annual per donee in 2024). Estate tax thresholds and Form 706 requirements.
Personal Tax Prep FAQs
What documents do I need to bring for a complex return?
For a comprehensive return, we typically need: W-2s and 1099s (income), 1099-B for investment transactions (usually from your brokerage), Schedule K-1 from any partnerships or S-Corps, year-end mortgage statements (1098), prior year tax return, rental income and expense records organized by property, and any IRS notices received during the year. We'll send you a custom document checklist once we know your specific situation.
Can you help if I haven't filed in several years?
Yes. Many clients come to us behind on filing — sometimes several years. We assess the situation, determine which years still need to be filed (the IRS typically assesses penalties for the most recent 6 years), gather the required documents, and file in the correct order. Most non-filers are not at risk of criminal prosecution if they voluntarily file and address any balance owed.
How do I report cryptocurrency correctly?
Every sale, trade, or exchange of cryptocurrency must be reported on Form 8949 and summarized on Schedule D. You'll need to know your cost basis for every transaction — the date acquired, the amount paid (in USD at time of purchase), and the date and amount of each sale. We can work from exchange transaction histories (CSV exports from Coinbase, Kraken, etc.) or specialized crypto tax software integrations.
Can I deduct my home office as an employee?
Post-2018 (Tax Cuts and Jobs Act), employees can no longer deduct unreimbursed work expenses — including home office — on their federal return. The home office deduction is only available to self-employed individuals (Schedule C) or certain pass-through entity situations. Some states (including California) still allow it on the state return; we check all applicable rules for your situation.
What if I receive a notice after my return is filed?
If you're our client, any IRS or state tax authority notice gets handled by us — at no additional cost for routine responses. We review the notice, determine if it's a processing error, information request, or proposed assessment, respond appropriately, and keep you updated. Most notices are resolved within 60–90 days.
Other Ways We Support Your Business
Complex Tax Situation? Let's Talk.
Rental income, investments, self-employment, cryptocurrency, multi-state — whatever your situation involves, we've handled it. Schedule a tax review and let's make sure your return is done correctly, completely, and on time.