Accounting
Opportunity zones and other gain deferral strategies save on taxes
Published
8 months agoon

Stocks, real estate and alternative assets are near their all-time highs amid an election year with an uncertain tax landscape looming. Investors are calling and seeking last-minute tax mitigation strategies. For clients who have big gains from appreciated assets, I often recommend the federal opportunity zone program because it’s the most flexible and most impactful tax deferral program I’ve seen in my 40-plus year career.
As of now, the OZ program is set to begin winding down in 2026. Absent
In a nutshell, the OZ program allows investors to defer their capital gains from sales of appreciated real estate, stocks, businesses, personal residences, collectibles and even crypto through 2026. They do so by investing in one of 8,700 distressed areas of the United States via a Qualified Opportunity Fund (QOF). They just need to make their investment within 180 days of the gain reporting date. If the gain is coming through a K-1, the start of the 180-day period can be delayed until March 15 of the year following the gain date. The QOF then deploys those gains into qualifying real estate or an operating business located within one of the 8,700 designated OZ census tracts. By keeping their invested gains in place, your clients won’t pay tax on those gains until at least April of 2027. Further, if they hold the investment for 10 years, all post-reinvestment appreciation from their original QOF investment will be excluded at the federal level — and at the state level in all but six states.
Bipartisan support
The OZ program has always had bipartisan support because it’s designed to spur economic growth in underserved areas. QOFs have raised an estimated $150 billion in equity since the program began in 2018 — far surpassing the most optimistic projections. Further, bipartisan legislation is pending to push out the gain deferral period from 2026 to Dec. 31, 2028. Proposed legislation would also bring back the basis step-ups of 10% and 5% that were part of the original program, but with shorter holding periods to qualify for the step-up — five years for the 5% step up and six years for the 10% step up.
Advantages of doing business in an opportunity zone
People typically associate OZ funds with real estate development, but about 25% of our OZ work involves operating businesses located within opportunity zone census tracts throughout the U.S. For your clients that are startups or existing businesses, there are many advantages to relocating to opportunity zones, such as more affordable real estate, rental rates and operating costs to help businesses save money.
To become a Qualified Opportunity Zone Business (QOZB), a business must meet the 50% Gross Income Test. There are three “safe harbors” within the regulations and the business must meet only one of them:
- At least 50% of the services performed (based on hours) by its employees or contractors are performed within the Qualified Opportunity Zone.
- At least 50% of the compensation paid to QOZ-based employees and independent contractors is performed in the QOZ.
- The core operations and facilities responsible for generating half of the business’s gross revenue are located within a QOZ.
Our firm works with many serial entrepreneurs, including tech gurus and engineers, who sell their family businesses, rental real estate or personal real estate, and then roll the gains into a QOF where they start one or multiple businesses within the QOZ. Many entrepreneurs are using a combination of real estate entities and operating businesses in their OZ Funds.
OZ for homeowners with big gains
In today’s real estate market, many homeowners are joyfully selling their residences for substantially more than they paid for their properties years or even decades ago. But after closing, they’re surprised to receive hefty capital gains tax bills on the appreciation over their first $500,000 in basis (married) or first $250,000 in basis (single). For instance, a married couple that bought their house for $200,000 30 years ago and sells it for $1 million today would have an $800,000 gain and would have to pay capital gains tax on $300,000, after claiming the $500,000 primary residence exemption ($1 million – $200,000 – $500,000). That’s a tax bill of $45,000 to $60,000 federal alone.
If the homeowners are in good health, then reinvesting the capital gain into a QOF can offer substantial tax savings. In the above example, they still have $700,000 in cash after making the QOF investment, assuming there was no mortgage.
OZ vs. 1031 exchange
The OZ program differs from a 1031 exchange in several ways. A 1031 exchange can only be used for real estate assets, whereas with the OZ program, the gain from the sale of any type of asset — real estate, stocks, bonds, collectibles, crypto, etc. — can be placed into a QOF and receive the tax benefits. Remember, the OZ program only requires your client’s gain to be placed into the QOF (not the full market value of the investment) to defer 100% of the gain. Then the QOF or a subsidiary QOZB invests in the property. Your client cannot invest in the property directly. Example: Let’s say you had $300,000 basis on a piece of land, and you sold it for $1 million (i.e., a $700,000 gain). To get the full deferral under a 1031, you’d generally have to buy a $1 million dollar piece of property. In the OZ world, you would only have to reinvest $700,000 to eliminate 100% of your gain.
Also, under the OZ program, all the depreciation you claim, including cost segregation and everything in the interim period never gets recaptured when you dispose of it after 10 years. That ends up boosting your ROI another 2% to 3% per year. Also, your clients have time to do a ground-up build in an OZ fund using deferred tax dollars. By contrast, with a 1031 they generally can’t do a ground-up build since they must purchase real estate with an equal or higher value to defer all their 1031 gain.
Installment sales
If your clients don’t want the complexity of an OZ fund, they can simply do an installment sale. They simply sell their land with a building on it and take back a seller note for part of it. Many people overlook the fact that even if they don’t collect $1 on the note in the year of sale, they are still stuck with 100% of the recapture that they have on the depreciation they’ve previously claimed. Therefore, they must be sure to collect enough to pay the tax on the depreciation recapture. The good news is they can defer the rest of the gain until the cash is collected. Their tax basis is allocated to each tranche of collections that they receive. Also, they run the risk that capital gain rates could be higher, and that’s also a risk in the OZ world. Vice President Harris just announced plans for a 28% capital gain rate (up from 20%) for taxpayers with incomes above $1 million. We don’t know the outcome of the upcoming presidential election, so we don’t know what the 2026 tax rates are going to be. Remember, the OZ program defers the capital gain reporting — not the tax.
Delaware statutory trust
The Delaware statutory trust is another vehicle enabling investors to move or shelter their capital gains. DSTs are essentially pre-packaged 1031s that allow multiple investors to pool their money and invest in actual real estate properties (not funds) without the headache of managing the properties, which are often institutional-grade assets such as apartment buildings, office buildings and shopping centers. This collaboration allows your clients to diversify their portfolios and potentially earn higher after-tax returns on their investments.
Regardless of which party wins the White House in November, tax rates are likely to be worrisome for many of your successful clients. It will become more concerning for them in a few years when the multi-trillion-dollar U.S. debt load can no longer be ignored. If your client has gains of $1 million or more from any type of appreciated asset, the OZ program — or one of the other tactics explained above — should be on your short-list of strategies for them to consider. Doing good for others while doing well for your clients and their families. That’s a win-win all around — exactly the intention of the bipartisan drafters of the OZ program.
You may like
Accounting
AI great at simple tasks but struggles with complexity
Published
5 hours agoon
May 9, 2025
Artificial intelligence has indeed led tech-forward firms (including those in this year’s
On the positive end, firms such as the Texas-based Franklin Alliance reported that adopting AI technology has dramatically increased their capacities as bots take on repetitive manual tasks with an ease and a speed far past more conventional automation setups, allowing accountants to focus more on higher value tasks.
“What’s been most impressive about the AI tools we’ve explored is their ability to dramatically reduce the time spent on repetitive, manual tasks—things like document summarization, data extraction, and even early-stage tax prep. In the right context, these tools create real efficiency gains and allow our team to shift focus to higher-value advisory work,” said Benjamin Holloway, co-founder of Texas-based Franklin Alliance.

madedee – stock.adobe.com
For some, like Illinois-based Mowery & Schoenfeld, these efficiencies have been most impressive on the internal administration side, with AI effectively taking care of the non-accounting work that nonetheless keeps many firms afloat, especially where it concerns meetings.
“Truly most impressive and a huge time savings for us has been AI’s ability to record and summarize Team meetings. Circulating notes and reducing administrative burden on such activities has freed up much capacity, both for our admin side and for partners or management who are not able to be at every meeting,” said Chris Madden, director of information technology.
Others, like top 10 firm Grant Thornton, emphasized AI’s benefits in client-facing activities and noted that it has been especially meaningful in its risk advisory services at least partially due to the firm’s recently-launched CompliAI tool, designed specifically for this area.
“The tool uses generative artificial intelligence and was developed using Microsoft technology, including Microsoft Azure OpenAI Service. CompliAI’s ability to quickly analyze vast datasets and identify potential risks has proven invaluable in combining Grant Thornton’s extensive global controls library with generative AI models and features, including AI analysis, ranking and natural language processing capabilities. As a result, our employees can run control design and assessment tasks in minutes, versus days or weeks. This means clients enjoy faster operational insights, which could amount to a new level of efficiency and a path toward transformative growth,” said Mike Kempke, GT’s chief information officer.
Another positive frequently mentioned, such as by top 25 firm Cherry Bekaert, has been the accessibility and ease of use for many AI solutions even for those without strong technical capacities. Assurance partner Jonathan Kraftchick said this means they did not need to wait long before they began seeing results.
“The most impressive aspect of AI has been its ability to add value with minimal ramp-up time. Many of the tools we’ve implemented have a low barrier to entry, allowing users to start experimenting and seeing results almost immediately. Whether it’s drafting content, conducting accounting research, summarizing meetings, normalizing data, or detecting anomalies, AI has consistently helped accelerate tasks and enable our teams to focus on higher-risk or higher-value areas,” he said.
Several firms, such as California-based Navolio & Tallman, also mentioned improvements to broad strategy and ideation, saying it’s been good for enhancing creativity and accelerating the early stages of their work.
“We’ve still seen value in AI as a jumping off point for ideas and strategy. It’s been helpful for brainstorming, drafting early versions of client communications, and supporting high-level planning conversations,” said IT partner Stephanie Ringrose.
Inconsistencies, inaccuracies, insufficiency, and insecurity
At the same time, firms over and over again said that while the strength of AI comes in handling simple jobs, it often lacks the precision and consistent accuracy needed for higher value accounting work. While it can certainly generate outputs at an industrial scale, trusting that those outputs are correct is another story for firms like Community CPA and Associates.
“AI is incredibly useful for certain types of tasks, such as summarization, data extraction, answering simple questions, drafting communications or documentation, brainstorming ideas, or serving as a sounding board. However, we have observed that most AI tools we’ve tried have difficulty with complex tasks that require lots of context, precision, or domain-specific knowledge. Oftentimes in these cases, AI tools will generate responses that are overly confident or wrong and are missing key information due to not being integrated with other systems or software we have,” said CEO Ying Sa.
Some, like top 25 firm Armanino, noted that these challenges mean that humans need to devote considerable time to ensuring the quality of AI outputs and intervening when the programs go off track.
“The primary disappointment stems from the occasional inaccuracies or biases inherent in AI-generated outputs, commonly referred to as ‘hallucinations,’ necessitating continuous human oversight to ensure reliability. Addressing these inconsistencies remains an ongoing challenge,” said Jim Nagata, senior director of cybersecurity and IT operations.
Top 25 firm Eisner Amper’s chief technology officer Sanjay Desai noted that these issues with accuracy and consistency can be found across AI solutions, though noted that the technology is still quite new and so many things are still in the process of being refined.
“The lows come from the gap between what’s possible and what works reliably in practice. We still need strong guardrails to define valid inputs and outputs, especially in sensitive use cases. Technologies like retrieval augmented generation (RAG) haven’t yet delivered the accuracy or consistency we need when working with proprietary or domain-specific data. Even in mature areas like audio-to-text transcription, we see issues—particularly with accurately identifying speakers in multi-person meetings, which affects the quality of recaps and follow-up actions. In short, while LLMs have come a long way, making them enterprise-ready still requires ongoing human oversight, thoughtful implementation, and continuous refinement,” said Desai.
Another issue reported by several firms was what firms like Navolio & Tallman saw as ongoing security risks from AI solutions that limits their ability to apply the technology to more sensitive use cases.
“The overall attention to security and privacy is still more limited than our industry requires, vendors have not yet aligned their pricing models with the impact their tools make to the business, and vendors still oversell their AI capabilities,” she said.
Top 25 firm Citrin Cooperman also noted–among other things–that the security of these solutions could stand to improve.
“The overall attention to security and privacy is still more limited than our industry requires, vendors have not yet aligned their pricing models with the impact their tools make to the business, and vendors still oversell their AI capabilities,” said chief information officer Kimberly Paul.
Another issue with AI that firms have reported is that solutions today don’t seem to integrate especially well with other programs, which limits the ability of these solutions to work across multiple systems in a single coherent workflow–under such conditions, AI solutions can wind up being siloed from the very areas it is needed the most.
“We believe one of the biggest gaps in current AI solutions is the inability to integrate into other AI solutions to work collectively across one process or workflow. There are many cases where one AI solution is very good at a specific task, while another is very good at another process or task, but the gap is the ability to integrate those solutions together to solve for an entirety of a process or a workflow,” said Brent McDaniel, chief digital officer for top 25 firm Aprio.
There is also the matter of data integration, which is needed for AI systems to gain a more holistic understanding of a firm’s needs. Without such integrations, AI becomes more limited in its ability to develop insights and provide actionable guidance, according to Tom Hasard, IT shareholder for New Jersey-based Wilken Gutenplan.
“We wish AI tools could fully synthesize all of our internal data and unique expertise—beyond the scope of general internet search—and provide detailed, context-specific answers for our team. In the near term, we envision an internal system that taps into our accumulated knowledge to assist staff in resolving complex client problems more quickly. Over time, this capability could be extended to give clients direct, on-demand access to our specialized insights, effectively scaling our expertise and delivering value in a more immediate and personalized way,” he said.
Beyond just data, lack of integration also limits the ability for AI to address complex problems due to lack of cross-disciplinary expertise, according to Kempke from Grant Thornton.
“Current AI solutions lack the deep cross-disciplinary expertise to be able to solve complex issues. AI today is optimized for specific fields and tasks but when it comes to solving problems that span multiple disciplines such as Tax, Legal and Finance, the current solutions are not yet capable of providing meaningful advice and guidance. Grant Thornton is already working with various AI partners on this issue and targets to be a very early adopter of the next iteration of AI that addresses this,” he said.
The AI wishlist
Many firms hoped that the next generation of AI solutions would address these sorts of problems in a way that will allow them to become true assistants capable of taking on complex tasks that require extensive judgment.
“We have found that AI currently lacks in the ability to replicate human creativity and complex decision-making. While AI excels at data analysis and task automation, it struggles with tasks requiring creativity and nuanced judgment. If AI could offer more sophisticated support in areas such as accounting and audit services, its value and impact in our daily lives would be significantly enhanced,” said Jim Meade, CEO of top 50 firm LBMC.
Desai, from Eisner Amper, also pointed out that AI isn’t very good at handling bad data, which is a problem considering that AIs run on data. This means that using AI effectively today still requires a great deal of data processing and sanitation to make information useful. If humans did not need to do so much manual cleanup to get data AI-ready, it would help make the technology even more efficient.
“One of the biggest gaps in AI today is its limited ability to handle bad data. Since data is the foundation of any AI strategy, it’s a challenge that most organizations still face— dealing with messy, inconsistent, or unstructured data. We wish AI could do more to identify, fix, and improve data quality automatically, instead of relying so much on manual cleanup,” said Desai.
Finally, Avani Desai, CEO of top 50 firm Schellman, said that AI needs to not only be safer, it needs to be visibly so, as trust and confidence in the technology is often key to adoption.
“I wish that AI could de-risk itself so that clients would be more open to using it and build client trust. If AI could more clearly demonstrate safety and responsible use, adoption would be much easier. Once people understand it’s here to help—and learn to use it responsibly—the fear will fade,” she said.

Representative Nicole Malliotakis said increasing the state and local tax deduction cap to $30,000 from $10,000 would reduce the tax burden of the vast majority of people in her district, indicating support for a proposal that is dividing Republicans.
“Every member needs to advocate for the particular needs of their district. Tripling the deduction to $30,000 will provide much-needed relief for the middle-class and cover 98% of the families in my district,” Malliotakis, a Republican representing Staten Island, New York and a member of the House tax committee, said in a statement to Bloomberg News on Friday.
Malliotakis’ nod of approval for a $30,000 SALT deduction cap comes as Republicans are fighting among themselves about how high to increase a tax break that has the potential to scuttle President Donald Trump’s entire tax package.
House Speaker Mike Johnson on Thursday said the $30,000 write-off limit is one of several options being discussed. That figure was rejected by several other New York Republicans, including Elise Stefanik, Nick LaLota, Mike Lawler and Andrew Garbarino. California’s Young Kim also rebuffed the idea.
Malliotakis’ district has less expensive property values and lower incomes than some of the other lawmakers pushing for a SALT expansion, making it politically viable for her to accept a lower cap than some of her colleagues.
White House Press Secretary Karoline Leavitt suggested on Friday that Trump would not weigh in on an appropriate level for a SALT cap, leaving it to lawmakers to resolve.
“There’s a lot of disagreement on Capitol Hill right now about the SALT tax proposal, and we will let them work it out,” she told reporters.
House Republicans’ narrow majority means that Johnson needs to win the support of nearly all his members to pass Trump’s tax-and-spending package.
Several of the SALT advocates have said that they are willing to block the bill unless there is a sufficient increase to the deduction. However, most members have not publicly stated how high the deduction must be to win their support.
The debate over SALT has proved to be a particularly thorny fight because it is a political priority for a small but vocal group of Republicans representing swing districts critical to the party maintaining a majority in the 2026 midterm elections.
Expanding the write-off is an expensive proposition, and Republicans have little fiscal wiggle room as they are sparring over ways — including cuts to Medicaid and levy hikes on millionaires — to offset the cost of the tax-cut package.
The House Ways and Means Committee is slated to consider the tax portion of the bill on Tuesday, including SALT changes.
Accounting
GOP eyes endowment tax hike in escalation of Ivy League feud
Published
7 hours agoon
May 9, 2025
House Republicans are considering increasing taxes on university endowments, a significant threat to some of the nation’s wealthiest schools as President Donald Trump seeks to tighten control over American higher education.
The measure is in a draft of the tax package Republicans are weighing, according to people familiar with the matter who spoke on condition of anonymity to share details on the effort. The proposal would create a tiered system of taxation so that wealthy colleges and universities pay more as the size of their endowment grows, the people said.
Republicans are considering boosting the 1.4% endowment tax currently on the books to rates as high as 14% to 21%, a person familiar with the matter said.
The bill is not finalized, however, the people cautioned, and the draft could change as Republicans negotiate its terms, a complex task as the party looks to renew and expand tax breaks and find ways to pay for them with only a narrow House majority.
Targeting university endowments would be a major escalation of Trump’s fight with elite colleges and universities, which has seen the administration demand changes to school policies that reflect his priorities.
The current tax on private-school endowments ensnares many of the richest universities, like Harvard University and Yale University, as well as smaller elite institutions such as Amherst College and Williams College. Some of the wealthiest private colleges in the country boast endowments of at least $500,000 per student.
Harvard, in particular, with a $53.2 billion endowment, has been locked in a high-stakes fight with the Trump administration over its demands for changes at the school. Harvard has sued several U.S. agencies and top officials for freezing billions of dollars in federal funding. Trump has also threatened the school’s tax-exempt status, though experts say revoking that designation would be a lengthy process involving the Internal Revenue Service and the courts.
A new
The poll found that 62% of Americans support maintaining federal research funding, 72% believe “liberals, students and professors can speak freely to at least some extent,” and 84% are concerned at some level about the cost of tuition, an issue Trump has not focused on.
Trump’s 2017 tax package, which Republicans are moving to renew, implemented an endowment levy of 1.4% on net investment income, similar to one that private foundations pay. That levy generated more than $380 million from 56 colleges or universities in 2023 — though it affected just a small fraction of the 1,700 private, nonprofit US schools.
House Budget Committee Chairman Jodey Arrington floated a long list of possible budget cuts in January that included raising $10 billion over 10 years by raising the endowment tax to 14%.
Discussions over the Republican tax package are reaching a critical stage. Trump is meeting Friday with the chair of the House Ways and Means Committee — the chamber’s tax-writing panel, according to people familiar.
Trump and Representative Jason Smith will discuss the draft proposal. The committee is expected to release parts of the bill later this afternoon and the rest of the draft on Sunday night or Monday, the people said.
One of the people familiar cast the effort as a bid by Republicans to ensure that universities spend their endowments on their students and not on other initiatives disfavored by conservatives, such as diversity, equity and inclusion efforts or on challenging the Trump administration’s policies.

AI great at simple tasks but struggles with complexity

Number of ‘tariff’ mentions has soared past ‘AI’ on earnings calls

How top tax rates compare, as Trump eyes hike for wealthy

New 2023 K-1 instructions stir the CAMT pot for partnerships and corporations

The Essential Practice of Bank and Credit Card Statement Reconciliation

Are American progressives making themselves sad?
Trending
-
Finance6 days ago
Warren Buffett to ask board to make Greg Abel CEO of Berkshire Hathaway at year-end
-
Finance1 week ago
Berkshire meeting ‘bazaar’ features Buffett Squishmallows, 60th anniversary book and giant claw machine
-
Personal Finance1 week ago
Millions of older workers lost jobs during Covid. Prospects have improved
-
Economics1 week ago
Why does America have birthright citizenship?
-
Personal Finance1 week ago
Why Roth conversions are popular when the stock market dips
-
Economics1 week ago
How Donald Trump could rescue John Roberts
-
Economics1 week ago
Jobs report Friday to provide important clues on where the economy is heading
-
Economics1 week ago
How one Ivy League university avoided the president’s wrath