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We Do Books™ Blog

Michael DiSabatino of We Do Books™ shares expert insights to help you unlock your business's full potential by delivering proven strategies for maximizing tax savings, streamlining operations, and driving sustainable growth.

The information provided on this site is for general informational purposes only and should not be construed as professional financial, tax, or legal advice. For advice tailored to your specific situation, we recommend consulting with a qualified professional. We Do Books is here to assist by calling 855-922-WeDo (9336)
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Michael DiSabatino

When One Dollar of Income Can Cost You $18,000: The ACA Subsidy Cliff Returns in 2026

ACA Subsidy Cliff 2026 concept showing health insurance money falling off a cliff with red downward arrow, illustrating risk of full premium tax credit repayment and financial loss under Affordable Care Act rules

ACA Subsidy Cliff 2026: How Exceeding 400% of Poverty Can Trigger Premium Tax Credit Repayment

Why a Small Income Miscalculation Could Trigger a Big Tax Bill

For several years, the Affordable Care Act (ACA) marketplace included a safety feature that helped taxpayers avoid catastrophic repayment of health insurance subsidies.

That protection is scheduled to expire after 2025, meaning the original ACA rules return beginning in 2026.

For taxpayers who carefully manage their income to qualify for premium subsidies, this change matters more than most people realize.

And unfortunately, we see the consequences every year in tax season.

Clients often receive advance premium credits based on income estimates provided during enrollment. If those estimates turn out to be wrong, the IRS reconciliation process can produce an unexpected tax bill.

Starting in 2026, the risk becomes significantly larger.

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Michael DiSabatino

529 Plans: The Tax Break Everyone Uses… But Few Use Well

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529 Plans: The Education Savings Tool Everyone Talks About… But Few Fully Understand

Let’s be honest. Saving for education has turned into its own little maze. Tax rules here, contribution limits there, and somewhere in the middle is a well-meaning parent just trying not to get steamrolled by tuition.

Enter the 529 plan. The fan favorite. The one everyone’s heard of… and half understand.

Let’s fix that. Here is a SIMPLIFIED, easy to understand overview of all you need to know...

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Michael DiSabatino

The IRS Fresh Start Program: Separating Fact from Gimmickry

Fresh-Start-Truths

IRS Fresh Start: The Reality Check

Don't let tax debt keep you in the dark. The IRS Fresh Start initiative offers genuine avenues for relief, but it’s not a magic trick. It requires careful navigation and compliance. Think of it as a well-lit path toward financial stability—if you have the right map.

While marketing emails might make it sound like an automatic "get out of debt free" card, the reality is that the program streamlines existing IRS tools, such as Offers in Compromise, Installment Agreements, and tax lien relief. To find your way through, you must meet specific criteria, provide detailed financial information, and stay current on future filings.

Success isn't about wishing your debt away; it’s about strategic action and professional guidance. Taking a reality check on your situation is the first step toward a clearer, secure financial horizon. Let WeDoBooks.com help you find the way.

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Michael DiSabatino

10 Sources of Tax-Free Income

Stack of US dollar bills tied with a red ribbon, symbolizing tax-free income, financial gifts, and money-saving opportunities

What Everyone Should Know

Wouldn't it be nice to have a source of nontaxable income?

You may be more fortunate than you realize.

Listed here are a number of income items that the IRS does not tax.

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Michael DiSabatino

Tax Surprises for the Newly Retired

An elderly couple from behind, slumped over a kitchen table covered in medical bills, tax forms, and retirement withdrawal notices. The scene uses warm, realistic lighting and features details like a prescription pill organizer and a circled wall calendar, conveying financial stress and aging.

You've got it all planned out. Your retirement savings accounts are full, you have started receiving Social Security benefits and your pension is ready to go. Everything is planned. What could go wrong?

Here are five surprises that can turn your plan on a dime.

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Michael DiSabatino

OBBBA: "No Tax on Tips" — What Actually Changes

OBBBA:

OBBBA adds a temporary, targeted deduction for tips. It is not a universal no tax on tips. Many tipped amounts are still taxable, and payroll taxes still apply.

Here is the clean, CFO-level breakdown:

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Michael DiSabatino

Net Unrealized Appreciation (NUA): A Little-Known Tax Strategy for Company Stock in Retirement Plans

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Net Unrealized Appreciation (NUA) concept with 401k jar, stacks of company stock, gold bull, U.S. flag, tax forms, and rising bar graph, illustrating a little-known tax strategy for retirement plan company stock.

Net Unrealized Appreciation (NUA): A Tax Opportunity Hidden Inside Some Retirement Plans

Many employees accumulate company stock inside their retirement plans over the course of their careers. When retirement approaches, that stock may qualify for a little-known tax treatment called Net Unrealized Appreciation (NUA).

When handled correctly, NUA can significantly reduce the tax burden associated with distributing company stock from a retirement plan. When handled incorrectly, the opportunity disappears and the entire distribution may become taxable as ordinary income.

Understanding the mechanics of NUA is therefore important before taking any action with employer stock held inside a retirement account.

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Michael DiSabatino

Do You Need to File a Tax Return?

Laptop and Form 1040 tax return next to a manila envelope with a blue sticky note question mark on a blue and yellow background, symbolizing uncertainty about whether you need to file a federal tax return.

Getting This Wrong Can Cost You

One of the more common tax questions is whether you need to file a federal tax return this year. The answer is: it depends. But not filing a tax return when you should can cost you plenty, especially with the passage of a major piece of tax legislation like the One Big Beautiful Bill Act. Here are some quick tips to help you determine your answer.

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Michael DiSabatino

NON-Retiree Retirement Ideas

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Want money when you retire?

Here are some tips.

Here are five common retirement planning tips and what you can do to take advantage of them. The key is retirement planning starts today, not decades from now when you are reaching retirement age.

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Michael DiSabatino

Your Home — A Bundle of Tax Benefits

Model home sitting on IRS Form 1040 tax documents with U.S. dollar bills, representing homeownership tax benefits, mortgage interest deductions, property tax deductions, and real estate financial planning.

There are many tax benefits built into home ownership. Here's a summary of the most common.

It may be worth a quick review to ensure you are maximizing your home ownership tax benefits.

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Michael DiSabatino

NEW FREE MONEY! — Trump Accounts for Kids

NEW FREE MONEY! — Trump Accounts for Kids

The New Child Savings Plan Parents Need to Know (530A / “Invest America”)

Congress has officially blessed us with yet another account type. This one is built for children and is commonly being called a “Trump Account” (also referred to as a Section 530A / “Invest America” account). The elevator pitch: it’s a tax-advantaged, long-term investment account for a minor, seeded (in some cases) with government money, and designed to push families toward early investing.

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Michael DiSabatino

2026 Gambling Taxes — The IRS Just Added a 10% "House Edge" to Your Losses

A confident man in a suit holding cash outside a brightly lit casino, symbolizing gambling winnings and looming IRS tax changes for 2026.

If you’ve gotten used to reporting gambling winnings and then “washing them out” with gambling losses on your tax return, 2026 is where that muscle memory can betray you. A federal law change effective for tax years beginning after December 31, 2025 rewrote the wagering-loss rule in IRC §165(d) so the deductible amount is now generally 90% of your wagering losses, and it’s still capped at your wagering gains (winnings). Translation: even a break-even gambling year can create taxable “phantom income” that you’re not accustomed to seeing.

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Michael DiSabatino

The Hobby Loss Rule — Rodeo Edition (Internal Revenue Code §183)

Bull rider competing in a high-intensity rodeo event, gripping tightly with one hand while a powerful bucking bull kicks up dirt inside an outdoor arena, surrounded by cheering spectators.

The IRS doesn’t care how exciting your rodeo belt buckle is… they care whether you’re engaged in the activity with the actual intent to make a profit.

If it’s a business, losses are deductible.

If it’s a hobby, deductions are limited and can’t create a net loss against other income.

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Michael DiSabatino

Five Big Tax Mistakes — Don't Let Them Happen to You!

Stressed taxpayer holding tax documents and cash at home, surrounded by receipts and laptop, highlighting common tax mistakes like retirement and bank forms.

Every year taxpayers are hit with tax surprises that could be avoided if they just knew the rules.

Here are five big ones that are easy to avoid with some simple planning.

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Michael DiSabatino

GREAT! You Have a Large Refund — Now What?

A close-up of a U.S. Treasury check on a laptop keyboard, symbolizing the moment of receiving a large tax refund.

For some reason, some believe it's better to receive than to give when it comes to filing taxes.

While that may help your savings account, it's not always a great idea. Here's why:

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Michael DiSabatino

Tax-Free Rental of Your Property

A friendly homeowner welcomes a couple arriving with luggage to a well-kept suburban home prepared for short-term rental during a local event. The scene shows a “Welcome Guests” sign, neatly folded towels, fresh flowers, and a laptop with a rental agreement, with a stadium visible in the background at golden hour.

Most income you receive is taxable income that is reported to the federal and state tax authorities. However, renting out your home or vacation property on a short-term basis can be done tax-free if you follow the rules.

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Michael DiSabatino

Gone Phishing?

A computer keyboard with the word “Phishing” in red on a key and a metal fish hook resting on the keys, symbolizing email scams and identity theft.

Each year the IRS publishes the top dozen tax scams it encounters over the prior year. One of them that makes an all too common appearance on their list is the phishing scam.

Here is what you need to know.

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Michael DiSabatino

Common Overlooked Taxable Events

Overhead view of a wooden desk illustrating seven common tax pitfalls, including gambling winnings with casino check and poker chips, CD statements, 1099-R retirement forms, gift tax receipt, mileage logs, unemployment insurance stamens, and cryptocurrency charts on a tablet, arranged in a dramatic, realistic setting.

Some issues fly under the radar until they trigger an unexpected tax return notice, penalty, or tax bill. What may seem like routine financial activity can quickly turn into a costly mistake if it’s reported incorrectly.

Below are seven commonly misunderstood tax situations that deserve careful attention before filing.

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Michael DiSabatino

Understanding Tax Terms — Head of Household

A realistic household scene illustrating an unmarried adult supporting a home with a dependent, showing bills, groceries, and tax forms. Warm, detailed, and inviting, capturing the essence of head of household responsibilities.

The tax term head of household is one of the more misunderstood tax phrases inside the U.S. tax code.

However, if your situation warrants head of household status, there are two big tax benefits:


First, a higher standard deduction.

Second, lower effective tax rates for virtually every income level.

This is great, but only if you qualify.

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Michael DiSabatino

Personal Exemptions Gone Plus $6,000 New Deduction

Elderly couple over 65 reviewing 2025 tax documents at a kitchen table with a laptop, papers, and calculator. Realistic, warm scene showing seniors managing finances and planning for a new senior tax deduction.

What Everyone Should Know

The recently passed One Big Beautiful Bill Act (OBBBA) addresses some tax law uncertainty while creating several benefits impacting your 2025 tax return. One of these benefits is a new $6,000 deduction for seniors. Here is what you need to know.

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