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Are Venmo, PayPal, and Cash App Payments Taxable? The 1099-K Rules for 2026
If you have sold anything on eBay, collected payments through Venmo, or used PayPal for freelance work, you may have heard that the IRS was about to start requiring platforms to send you a tax form for transactions over $600. Congress repealed that rule in July 2025, and the reporting threshold is back to where it was before 2021. What has not changed is the underlying tax obligation. Whether or not you receive a Form 1099-K, income you earn through these platforms is general
Gregg Jaffe
4 days ago6 min read


Selling Your House on Long Island: What the Tax Bill Could Look Like
Long Island home prices have risen sharply over the past decade. Nassau County median sale prices are running roughly $852,000 as of spring 2026. Suffolk is around $715,000. For homeowners who bought fifteen or twenty years ago, the gap between what they paid and what they can sell for has grown into a number that carries real tax consequences. Most homeowners know there is a federal tax break on profits from the sale of a primary residence. Fewer people know exactly how it w
Gregg Jaffe
Jun 296 min read


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
Gregg Jaffe
Jun 14 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
Gregg Jaffe
May 45 min read
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