GENERAL TAX FAQ

Q: When do I need to file my tax return?

The federal individual tax deadline is typically April 15, unless extended by the IRS. Extensions give you until October 15, but any tax due must still be paid by April 15 to avoid penalties.

Q: Do I really need a tax professional?

If you have a business, rental property, investments, dependents, multiple states, or simply want to avoid mistakes, a tax professional can often save you more than the cost of the preparation.

Q: What documents do I need to give you?

Most clients need:

• W-2s
  
  

• 1099s
  
  

• Mortgage interest statements
  
  

• Brokerage statements
  
  

• Business income/expenses
  
  

• Rental property info
  
  

• Health insurance forms
  
  

• Estimated tax payment history
  
  

If you're unsure, we will provide a customized checklist for your situation.

Q: How long does it take to prepare my return?

Once we have 100% of your documents, most returns are completed within 5–20 business days, depending on complexity.

❓ REFUNDS & PAYMENTS

Q: How long will my refund take?

Most refunds take 1–3 weeks once the IRS accepts the return.
Paper checks and amended returns take longer.

Q: What if I owe taxes?

You must pay by April 15 to avoid interest and penalties.
We’ll provide vouchers and online payment instructions.

Q: Does filing an extension increase my chance of an audit?

No — extensions do not increase audit risk.
Many high-income and business clients routinely file extensions.

❓ DEDUCTIONS & CREDITS

Q: What expenses are tax deductible?

It depends on your situation, but common deductions include:

• Mortgage interest
  
  

• Property taxes
  
  

• Charitable contributions
  
  

• Student loan interest
  
  

• Business or self-employment expenses
  
  

• Health insurance (self-employed)
  
  

• Medical expenses (over 7.5% of income)
  
  

We help identify every deduction you're legally entitled to.

Q: Are GoFundMe donations deductible?

Only if the recipient is a registered 501(c)(3) nonprofit.
Personal fundraisers are not tax deductible.

Q: What home improvements are deductible?

Regular home improvements are not deductible, but improvements to rental properties are. Some energy-efficient upgrades may qualify for a tax credit.

❓ SELF-EMPLOYMENT & SMALL BUSINESS

Q: What can I deduct as a self-employed individual?

Common deductions include:

• Home office
  
  

• Mileage or vehicle expenses
  
  

• Equipment, supplies, and tools
  
  

• Insurance
  
  

• Marketing
  
  

• Business meals
  
  

• Professional fees
  
  

We review all categories to ensure compliance.

Q: Should I form an LLC or S-Corp?

It depends on:

• Your income level
  
  

• Liability needs
  
  

• Payroll requirements
  
  

• Long-term goals
  
  

An S-Corp may save taxes, but only when income reaches certain thresholds. We will evaluate your exact situation.

Q: Do I need a business bank account?

Yes — separating business and personal finances helps reduce audit risk and simplifies bookkeeping.

❓ RENTAL PROPERTIES & REAL ESTATE

Q: What can I deduct for my rental property?

Typical deductions include:

• Mortgage interest
  
  

• Property taxes
  
  

• Depreciation
  
  

• Repairs & maintenance
  
  

• Utilities
  
  

• Insurance
  
  

• Management fees
  
  

• Mileage
  
  

• Supplies
  
  

We also ensure proper depreciation schedules.

Q: What is depreciation?

Depreciation is a tax deduction that spreads out the cost of property over time.
Residential rentals depreciate over 27.5 years.

Q: Do I pay taxes when I sell a property?

You may owe capital gains tax and depreciation recapture — but planning ahead may help reduce or defer your tax.

Q: What is a 1031 Exchange?

A strategy that allows you to defer capital gains taxes by reinvesting sale proceeds into another property.

❓ TRUSTS & ESTATES

Q: Do I need to file a tax return for a trust or estate?

If the trust or estate earns $600 or more, a Form 1041 must be filed.

Q: Are inheritances taxable?

Generally, inheritances are not taxable income.
But assets inside estates or trusts may generate taxable income.

Q: Does Massachusetts have an estate tax?

Yes — Massachusetts has one of the lowest estate tax thresholds in the country.
We can help determine if the estate requires a return.

❓ MULTI-STATE TAXES

Q: Do I need to file taxes in more than one state?

You may need multi-state filings if you have:

• A business operating in multiple states
  
  

• Remote work income
  
  

• Rental properties
  
  

• Investment income sourced to another state
  
  

We handle multi-state tax issues nationwide.

❓ NOTICES & IRS ISSUES

Q: I received a letter from the IRS — what do I do?

Send it to us right away.
Most IRS letters are routine and can be resolved easily with proper guidance.

Q: Can you represent me in an audit?

Yes. Enrolled Agents have unlimited rights to represent taxpayers before the IRS.

Q: What if I haven’t filed taxes in years?

We help clients get back on track safely and discreetly.
The IRS often looks favorably on voluntary compliance.

❓ BOOKKEEPING & ACCOUNTING

Q: What’s included in monthly bookkeeping?

• Transaction categorization
  
  

• Bank reconciliations
  
  

• Financial statements
  
  

• Year-round support
  
  

• Tax-ready records
  
  

Q: Do I need bookkeeping if I only prepare taxes once a year?

Accurate books reduce errors, lower audit risk, and ensure you claim all allowable deductions.