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Real Estate Investor Tax Guide 2026: What the One Big Beautiful Bill Changed and What You Should Do About It
The One Big Beautiful Bill Act — signed July 4, 2025 — is the most significant tax law for real estate investors since 2017. If you own rental property, flip houses, or invest in commercial real estate, nearly every tool in your tax toolkit just got upgraded, made permanent, or both. This guide covers every OBBBA provision that affects real estate investors, with the dollar-specific examples and Indiana angles you won't find in a national summary. If you already read our blog
John Schaaf
5 days ago10 min read


Trump Accounts vs. 529 Plans vs. Roth IRAs
If you have children under 18, you've probably heard about Trump Accounts — the new tax-advantaged savings accounts created by the One Big Beautiful Bill Act. Children born 2025–2028 even get a free $1,000 government deposit. With accounts officially opening July 4–5, 2026, Indiana parents are asking us the same question: how does this compare to a 529 plan or a Roth IRA?
John Schaaf
Apr 812 min read


Hiring Your Kids in Your Business: The Complete 2026 Tax Guide for Indiana Families
If you own a small business and have kids, this might be the most valuable tax strategy you're not using. When done correctly, you can deduct your child's wages at your tax rate, your child pays little or no tax on those wages, and the money stays in the family. It's one of the few places in the tax code where the same dollar can be both deductible and (effectively) tax-free. But the rules differ significantly depending on your business structure, your child's age, and how m
John Schaaf
Apr 38 min read


The One Big Beautiful Bill: 8 Tax Changes Every Indiana Family and Business Owner Should Know
The One Big Beautiful Bill Act was signed into law on July 4, 2025 — and it's already changing how you file your 2025 return. The new deductions were never built into your withholding, which means many taxpayers overpaid throughout the year and are now seeing larger refunds. Here are the 8 provisions that matter most to our Indiana clients, what you need to do about them, and a few traps to avoid. One important note before we start: The new deductions for overtime, tips, c
John Schaaf
Apr 17 min read


How to Use Depreciation & Cost Segregation to Save Big on Your Real Estate Taxes
You own a rental property that makes money every month. What if we told you it could also show a loss on your tax return — and that loss could reduce what you owe on your other income? That's the power of depreciation and cost segregation. Here's how it works and what you need to know before using it. What Is a Cost Segregation Study? When you buy a rental or commercial building, the IRS makes you depreciate it over 27.5 years (residential rental) or 39 years (commercial)
John Schaaf
Mar 183 min read


The HSA: The Best Tax-Savings Vehicle
In our opinion, the Health Savings Account is the single best tax-savings vehicle in existence. Nothing else gives you all three of these at once: You deduct what you contribute — up to $8,750 for a family in 2026, plus an additional $1,000 catch-up contribution if you are age 55 or older. The money grows tax-free inside the account. You don't pay tax when you withdraw it for medical expenses. No other account does all three. Traditional IRAs and 401(k)s give you a deducti
John Schaaf
Mar 164 min read


How to Turn Rental Property Losses Into a Tax Advantage
Owning rental property comes with real costs — maintenance, vacancies, and financing. But here's what many owners don't realize: those losses can be one of your most powerful tax tools, if you know how to use them. The $25,000 Rental Loss Deduction If your modified adjusted gross income (MAGI) is under $100,000, the IRS allows you to deduct up to $25,000 in rental losses against your regular income each year — meaning those losses can directly reduce what you owe on your W
John Schaaf
Mar 112 min read


IRS Moves Toward All-Electronic Refunds: What you need to know
The federal government is eliminating paper checks in favor of electronic payments, though most taxpayers won’t be affected since 93% already use direct deposit. An executive order requires federal agencies to transition to electronic funds transfer, and the IRS began phasing out paper refund checks for individuals on September 30, 2025. Taxpayers who file without banking information may face delays and additional steps, and while alternatives exist for those without bank acc
christina4422
Jan 131 min read


USPS Postmark Changes: Don't miss your tax deadline
Effective Dec. 24, 2025, USPS will define the postmark date as the date of first automated processing, which may be later than the drop-off date. Because tax filings are considered timely only if postmarked on or before the due date under IRC §7502, taxpayers should mail documents at least two days early or obtain a manual postmark at a USPS retail counter, or use Certified or Registered Mail. For example, dropping mail in a box at noon on the 15th could result in a postmark
John Schaaf
Dec 23, 20251 min read


Don’t Waste a Family-Member’s 0% Federal Tax Bracket
If you have a family member with low income, they may be able to pay no Federal tax when selling stock that has been held for over 1 year. Assume you have a 25 year old child with little income and you have a large gain in a stock or security you hold. Instead of selling the stock, paying tax on it, and giving the child money, consider gifting the appreciated stock or security to your child and having them sell it. If you do, your child might be able to sell the stock, and
John Schaaf
Dec 3, 20251 min read


Have Appreciated Stock to Donate?
Assume you bought a stock for $5K that has appreciated to $30K. If you sell the stock and donate $30K to charity, then you have to recognize $25K of gain and might be able to deduct some or all of the $30K if you itemize. Instead of selling the stock and donating cash, consider donating the stock to charity and telling them to sell it to generate the cash they need. If you do, then you don’t recognize any of the gain and still might be able to deduct some or all of the $30
John Schaaf
Nov 24, 20251 min read


Want to pay 0% Tax on Stock Sales?
You can pay no Federal tax on the gain recognized from the sale of stocks and securities held for over 1 year to the extent you make less than around $124K as a married couple this year. So, if you are married and have joint income of $100K this year, you can sell stocks and recognize long-term capital gain of around $24K and pay no Federal tax on it. Any gain over $24K would be taxed for Federal purposes. When consider taking advantage of this, be aware that the extra inc
John Schaaf
Nov 24, 20251 min read


Want to Get a Deduction for Purchasing a 2nd Home?
You normally don’t get a deduction for the purchase of a 2 nd home that you use for personal purposes. If you want to change that, then buy the home this year, get it rented out as an AirBNB or VRBO at least 2 times with average customer stays of 7 days or less and spend 100 hours this year dealing with the home. If you meet these tests, then you normally can deduct 100% of the cost of furnishings and around 25% of the cost of the home this year. After the year is over, y
John Schaaf
Nov 17, 20251 min read


Prepay Rent to Yourself
Assume you operate your business as an S Corp and personally own 100% of the building you rent to the S Corp. If you’ve had an unusually high profit this year, you can use the “mailbox rule” to accelerate next year’s rent deduction. On December 31, your S Corp can write a check for 12 months of rent and place it in the mail. This allows the S Corp to take the rent deduction in the current year. When you receive the check in your mailbox on January 2 of the following year, the
John Schaaf
Nov 17, 20251 min read


Last Minute Year-End Business Tax Deductions
If you had an unusually large profit this year, consider: Prepaying up to 12 months of next year’s expenses, like rent or insurance – you can’t make a deposit towards next year’s expenses, but if you legally owe the money already and can pay it this year, then pay it Stop billing customers, clients, and patients Buy office equipment Remember, whatever you charge to your credit card this year for your business is a deduction this year Make a large inventory purchase this year
John Schaaf
Nov 12, 20251 min read


A Neat Crypto Trick
Cryptocurrency is not subject to wash sale rules like stocks are. Lets say you bought a coin for $10 and it is worth $5 and you want to continue to hold the coin. Sell the coin this year and recognize a loss of $5 that you can deduct, then immediately repurchase the coin for $5. You can use this $5 loss that you recognized to offset other gains or income you had this year. Contrast this with a stock: when you sell a stock and then re-purchase it within 30 days, you can’t
John Schaaf
Nov 12, 20251 min read


Buying Windows, Doors, Insulation, HVAC, or a Hot Water Heater for your Home?
The Federal tax credit for making most normal energy-efficient improvements to your home will expire at 12/31/2025. If you were planning on making these improvements soon, see if you can get them installed by 12/31/25. The credit for certain items or groups of items maxes out at 3.2K in 2025.
John Schaaf
Nov 10, 20251 min read


No Tax on Overtime – How Does that Work?
If you make under 150K single or 300K joint, then you don’t have to pay tax on the ½ of your time-and-a-half. The non-taxable amount of overtime is 12.5K per person if they qualify. This is effective for all of 2025.
John Schaaf
Nov 10, 20251 min read


No Tax on Tips – How Does that Work?
If you make under 150K single or 300K joint and work in normally-tipped industries, then you might not have to pay tax on tips reported to you on a W-2, 1099, or other tax-reporting form. The deduction is 25K per person if they qualify. This is effective for all of 2025.
John Schaaf
Nov 5, 20251 min read


529 Accounts Now Can be Used for More Expenditures
Originally, you could use 529 funds tax-free for college expenses only. Now you can also use them for K-12 education, homeschool expenses, exam prep, exam fees, student loan repayments, Roth rollovers, computers, books, trade school, K-12 tutoring, and professional credentialling….basically everything related to lifetime education. There are certain limits on some items, but the list is a lot longer than it used to be. For Indiana taxpayers, there is now less reason than e
John Schaaf
Nov 5, 20251 min read
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