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Quarterly Estimated Taxes: What the Self-Employed Need to Know Before June 15
If you are self-employed, a freelancer, or running a business where no one is withholding taxes from your income, the IRS expects you to pay as you go. That means quarterly estimated tax payments, and the second one for 2026 is due June 15. Most people who are new to self-employment are surprised by this. When you had a W-2, your employer sent money to the IRS every pay period. Nobody does that for you now. If you wait until April to settle up for the full year, you may owe a
Jim O'Callaghan, CPA
4 days ago4 min read


You Missed a Year. Or a Few. Here Is How to Get Back on Track.
Most people who have an unfiled return know they have one. They are not avoiding it because they do not care. They are avoiding it because they do not know where to start, and every month that passes makes starting feel harder. Whether you missed one year a while back or have not filed in several years, the process is the same: get the returns filed, address what you owe, and put it behind you. The IRS is generally more willing to work with people who come forward than with p
Jim O'Callaghan, CPA
May 45 min read


Filing a Tax Extension in New York: More Time to File, Not More Time to Pay
If your tax return is not ready by early April, filing an extension is the right call. That's not unusual, and it's not a red flag. Millions of taxpayers file extensions every year, and the IRS treats them as routine. What matters is understanding what an extension actually does, and just as important, what it does not do. The Deadline That Does Not Move Filing an extension moves your return deadline from April 15 to October 15. It does not move your payment deadline. If you
Jim O'Callaghan, CPA
Apr 34 min read


What We’re Seeing So Far This Tax Season (And What It Means for You)
March is when tax season stops feeling theoretical. The early filers are done, the procrastinators are starting to feel pressure, and many people are realizing their return is not as simple as they expected. At TaxMaster, we work with individuals, families, seniors, homeowners, and business owners across Queens and Long Island. By March, the same issues tend to surface year after year. This year, the One Big Beautiful Bill Act (OBBBA) has added a few new points of confusion.
Jim O'Callaghan, CPA
Mar 23 min read


How the One Big Beautiful Bill Act Could Affect Your 2025 Tax Return
If your taxes have felt unpredictable the last few years, you are not imagining it. The One Big Beautiful Bill Act, signed into law on July 4, 2025, introduced several changes that affect 2025 tax year rules , which most people are filing now or preparing to file. Some of these changes may lower taxable income. Others affect which deductions make sense or what documentation is required. A few do not change how much you owe at all, but they can slow down filing if you are not
Jim O'Callaghan, CPA
Feb 114 min read


Tax Season Is Here: What You Should Be Gathering and Looking For
Tax season has a way of arriving whether you feel ready or not. Once January turns into February, deadlines feel closer, questions pile up, and missing paperwork suddenly becomes stressful. The good news is that a little preparation now can make the entire process smoother, faster, and far less frustrating. Whether you are filing as an individual, running a small business, or doing a mix of both, gathering the right documents early helps avoid delays, reduce errors, and preve
Jim O'Callaghan, CPA
Jan 83 min read


SALT Deduction Cap Increase in 2025: What New York Homeowners Need to Know
If you own a home in New York, you know how heavy the tax load can feel. Between property taxes, state income taxes, and the high cost of living, every dollar matters at tax time. Since 2018, the federal SALT deduction cap has limited most taxpayers to a maximum of 10,000 dollars. For many families in Queens and Long Island, that cap has been a real financial hit. The One Big Beautiful Bill Act (OBBBA) changes that starting with the 2025 tax year. The expanded SALT deduction
Jim O'Callaghan, CPA
Dec 8, 20254 min read


Understanding the Standard Deduction Under the OBBBA: What New Yorkers Need to Know
The standard deduction isn’t just a line on your tax return — it’s one of the biggest factors in how much of your income actually gets taxed. With the One Big Beautiful Bipartisan Act (OBBBA) extending and expanding many provisions from the Tax Cuts and Jobs Act (TCJA), millions of taxpayers will see higher standard deduction amounts for the 2025 tax year (returns filed in 2026). That’s good news for most individuals and families across New York, especially those looking to
Jim O'Callaghan, CPA
Nov 10, 20254 min read


Year-End Tax Planning: What to Do Before December 31 to Reduce Your 2025 Bill
The last few months of the year aren’t just for holidays and celebrations—they’re also the final chance to lock in real tax savings. Once...
Jim O'Callaghan, CPA
Oct 7, 20254 min read


Key TCJA Provisions Made Permanent in OBBBA
When the House passed the "One Big Beautiful Bill Act" (OBBBA) in May 2025, it marked a pivotal moment for tax policy. Several key...
Jim O'Callaghan, CPA
Sep 10, 20252 min read


Summer Side Hustles and the IRS: What You Need to Know Before You Get Paid
As temperatures rise, so does the appeal of picking up extra income. From tutoring and landscaping to freelance design and weekend event...
Jim O'Callaghan, CPA
Aug 1, 20253 min read


How to Fix a Mismatched W-2 or 1099 Before It Triggers an IRS Notice
Tax season brings plenty of paperwork, including W-2s, 1099s, and other income documents. But if the information on your tax return...
Jim O'Callaghan, CPA
Jul 9, 20253 min read


What to Do If You Receive an IRS Notice
An unexpected letter from the IRS can be unsettling, but it doesn’t always mean there’s a major problem. Every year, millions of...
Jim O'Callaghan, CPA
Jun 13, 20252 min read


Facing Tax Challenges Head-On: Common Issues and Smart Solutions
Tax season can be stressful, especially for individuals, families, and small business owners managing a range of financial...
Jim O'Callaghan, CPA
May 12, 20253 min read


Found a Mistake or a Surprise 1099 After Filing? Here's What to Do
Filing your taxes feels like a big win—until a surprise 1099 shows up or a mistake comes to light.
Jim O'Callaghan, CPA
Apr 7, 20253 min read


Maximizing Tax Benefits for Small Business Owners
Effectively managing tax obligations is crucial for small business owners aiming to maximize profitability
Jim O'Callaghan, CPA
Mar 10, 20254 min read


Tax Filing Options: DIY vs. Professional Assistance
Navigating the complexities of tax filing requires careful consideration of whether to handle the process independently or seek assistance.
Jim O'Callaghan, CPA
Feb 6, 20252 min read


Essential Tax Documents Checklist for 2024 Filings
Stay organized for the 2024 tax season with this essential tax documents checklist. Learn how to maximize deductions, ensure compliance, and
Jim O'Callaghan, CPA
Jan 7, 20254 min read


Holiday Spending and Tax Deductions: What You Need to Know
The holiday season often brings a flurry of activity, from shopping for gifts to hosting gatherings. While the spirit of giving is at its...
Jim O'Callaghan, CPA
Dec 5, 20243 min read


Understanding the Tax Implications of Real Estate Transactions
Real estate transactions are significant financial events that come with various tax implications. Whether you are buying, selling, or...
Jim O'Callaghan, CPA
Nov 1, 20243 min read
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