Field notes
from the tax code.
Strategy, warnings, and the occasional rant — written by people who actually file returns for a living.
Quarterly Estimated Taxes for NY & NJ Freelancers (2026)
A plain-English guide for NY and NJ freelancers on paying quarterly estimated taxes. Learn who pays, when, and how to avoid costly IRS and state penalties.
Aug 23, 2026 · 7 min read
Got an IRS CP2000 Notice? Here's What to Do Next
Received an IRS CP2000 notice? Don't panic. It's not a bill or an audit, but you must respond. Learn what a CP2000 is and what your next steps are.
Aug 19, 2026 · 7 min read
Lowering Next Year's Tax Bill Now
Use your 2025 return as a diagnostic tool: calibrate withholding, max out new 2026 retirement limits, and spring-clean your tax strategy before year-end.
Aug 18, 2026 · 14 min read
Tax Changes When You Become Your Own Boss
Going from W-2 to self-employed means you pay both halves of Social Security and Medicare, make quarterly estimates, and unlock new deductions. Here's the full roadmap.
Aug 18, 2026 · 12 min read
Should You Adjust Your Withholding After Tax Season?
A big refund is an interest-free loan to the IRS; a big bill can trigger penalties. Here's how to tune your Form W-4 in 2026 to keep your money in your pocket.
Aug 18, 2026 · 13 min read
Do You Have to Pay Taxes on Sports Betting?
The IRS treats every sports betting payout as ordinary income — even if you never received a tax form. Here's how the new 2026 loss-deduction rule changes the math.
Aug 18, 2026 · 11 min read
Do I Pay Taxes on My World Cup Airbnb?
Hosting fans for the 2026 World Cup can be profitable — but the IRS treats your Airbnb or VRBO income as taxable once you cross 14 rental days. Here's how to keep more of what you earn.
Aug 18, 2026 · 12 min read
Will Marriage Lower My Tax Bill?
For most couples, saying "I do" unlocks better tax breaks, wider brackets, and doubled deductions. But high earners and some low-income families can face a marriage penalty.
Aug 18, 2026 · 10 min read
Can I Claim Education Expenses for My College Student?
The American Opportunity Tax Credit can put up to $2,500 per year back in your pocket for each eligible student — and can even land you a refund check.
Aug 18, 2026 · 10 min read
How New IRA Tax Rules Could Cost Your Heirs
SECURE 2.0 forces most non-spouse heirs to empty an inherited IRA within 10 years — and many now face annual RMDs. Here's how to protect your legacy.
Aug 18, 2026 · 11 min read
What Digital Asset Moves are Taxable?
The IRS treats crypto as property. Selling, swapping, spending, and staking all have tax consequences — wallet transfers don't, but your records still have to prove it.
Aug 18, 2026 · 10 min read
New 2026 Tax Rules for Charitable Giving
The OBBBA gives non-itemizers a $1,000/$2,000 above-the-line write-off — and hands itemizers a new 0.5% AGI floor. Here's how to give without losing deductions.
Aug 18, 2026 · 9 min read
When The Godfather Came to Town
A private fundraising night with special guest Gianni Russo — music, stories, signed memorabilia, and a room that gave generously.
Jul 24, 2026 · 3 min read
Lowering Next Year's Tax Bill — Now
The moves you make in May matter more than the ones you make in April. Here's how to start the clock on next year's return today.
May 12, 2026 · 6 min read
Filed an Extension? Avoid These Mistakes
An extension is more time to file — not more time to pay. Here's the fine print most people miss.
Apr 18, 2026 · 4 min read
The Not-So-Obvious AI Tax Scams
AI voice cloning, hyper-realistic phishing, and fake preparer sites are making tax scams harder to spot. Here's how to verify who you're really talking to.
Aug 18, 2026 · 14 min read
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