Deadlines and basics
- When Are Taxes Due This Year?
April 15, 2027 for 2026 returns, plus the other dates to know. - How Do I File a Tax Extension, and Does It Give Me More Time to Pay?
Six more months to file. Not more time to pay. - How Much Do I Have to Make to Be Required to File?
The income limits, and when filing makes sense anyway. - How Long Should I Keep My Tax Records?
Three years for most people, with some longer exceptions. - Does Florida Have a State Income Tax?
No, but there are a few things Floridians still need to know. - How Do Tax Brackets Work?
Why a higher bracket only taxes the extra dollars. With a free calculator.
Behind or owing
- How Far Back Do I Have to File If I Haven't Filed in Years?
Most people only need to file the last six years. - I Can't Pay What I Owe the IRS. What Are My Options?
File on time anyway, then set up a payment plan. - I Got a Letter From the IRS. What Does It Mean?
Find the notice number, check it's real, and answer by the date. - What Happens If I Don't File My Taxes?
Penalties, IRS-made returns and collection. And how to fix it. - Why Do I Owe Taxes This Year When I Usually Don't?
The usual reasons, and how to keep it from happening again. - How Do I Get My IRS Transcript or Last Year's AGI?
Online in minutes, by mail, or we can pull it for you.
New tax law
- Is There Really No Tax on Tips? How the Tips Deduction Works
A new deduction of up to $25,000 in tips, starting with 2025 returns. - Is There Really No Tax on Overtime? How the Overtime Deduction Works
A deduction for the extra half of time-and-a-half pay. - Is Social Security Tax-Free Now? The New Senior Deduction, Explained
A new $6,000 deduction for people 65 and older. - Tax Help for The Villages, FL
Social Security, the senior deduction and moving from up north, for Villages residents. - Can I Deduct My Car Loan Interest Now?
Yes, for some new cars bought in 2025 or later.
Gig and self-employed
- Do I Have to Report Venmo, PayPal or Cash App Money?
Business income is taxable either way; money from friends isn't. - Do I Have to Pay Quarterly Estimated Taxes?
If you'll owe $1,000 or more, probably yes. - How Much Should I Set Aside From 1099 or Gig Income?
A simple rule of thumb, and why it's more than people expect. - What Can I Deduct as a Delivery or Rideshare Driver?
Mileage is the big one. Here's what else counts.
Business owners
- Starting a Business in Florida: The Tax Steps
Structure, EIN, Sunbiz, sales tax and good habits from day one. - Should I Elect S Corporation Status?
When it saves money, and the salary rule that comes with it. - Hiring Your First Employee in Florida
Employee or contractor, payroll taxes and Florida's new-hire rules. - Closing a Business: The Tax Checklist
Final returns, final payroll forms and closing your Florida accounts. - Selling a Business: How the Sale Is Taxed
Asset vs. stock sales, and why the price split matters.
Life and paycheck
- Is Social Security Taxable?
It depends on your other income. Here's how to tell. - How Do I Fix My Withholding So I Don't Owe?
Use the IRS estimator, then give your employer a new W-4.
Investments and property
- What Is a 1031 Exchange, and How Is It Reported?
Swapping one investment property for another and putting off the tax. - Depreciation and Depreciation Recapture, Explained
Why you deduct a building over time, and pay some of it back when you sell. - How Is Crypto Taxed?
When it's taxable, when it isn't, and the new Form 1099-DA. - How Are RSUs and ESPP Shares Taxed?
Taxed as pay when they vest, and the 1099-B mistake that leads to double tax. - What Is a DST (Delaware Statutory Trust), and How Is It Taxed?
How DST income, sales, and 1031 basis and depreciation show up on your return. - Capital Gains Tax: Short-Term vs. Long-Term
Why holding more than a year matters, and how losses help. - What Is a K-1, and Why Does It Come So Late?
Your share of a partnership, S corporation or trust, and what to do with it. - Do I Pay Tax When I Sell My Home? The $250,000 / $500,000 Exclusion
Most homeowners owe nothing. Here's when you might. - Rental Property Taxes: The Basics
What to report, what to deduct, and short-term rental rules. - I Inherited Stock or a House. What's My Cost Basis?
Step-up in basis, and why inherited IRAs work differently.
Want a quick estimate? Try our free tax calculators.
Own a small business? Visit our Business Owner Center.
Own a DST or did a 1031 exchange? Visit our DST & 1031 Owner Center.
Also see: questions about working with us and our IRS notice pages for CP2000, CP59 and CP3219A.
Disclaimer: This page is general information, not tax advice. Every situation is different, and tax rules change. Reading this page doesn't make you a client.