The estate planning landscape transformed fundamentally on July 4, 2025, when the One Big Beautiful Bill Act was enacted into law. For ultra-high net worth families holding closely held businesses, significant art collections, or valuable collectibles, this legislation created both unprecedented opportunities and new compliance complexities. 

The 60th Annual Heckerling Institute on Estate Planning, held in January 2026, revealed that leading practitioners are now helping clients navigate a post-sunset world where the permanent federal estate and gift tax exemption of $15 million has replaced eight years of transfer tax uncertainty with a new mandate: strategic precision.

This article outlines the essential questions that owners of family enterprises, fine art, and collectibles should be raising with their professional advisory teams in 2026 and beyond.

Family business succession: QSBS, entity structure, and the new planning paradigm
The OBBBA significantly expanded the Qualified Small Business Stock exclusion under Internal Revenue Code Section 1202 for realized capital gains on the sale of qualifying stock, raising the per-taxpayer exclusion limit to $15 million and reducing the holding period for partial exclusions to three years, provided the stock is issued by a qualified C Corporation meeting all Section 1202 requirements. 

For family business owners, this creates what practitioners are describing as a significant planning opportunity – the ability to potentially shelter hundreds of millions in capital gains through sophisticated trust stacking and exclusion optimization strategies.

Questions to ask your advisors
Does our current corporate structure maximize QSBS eligibility under IRC Section 1202, and what restructuring, if any, might be warranted before any liquidity event? The Section 1202 requirements, including the active business requirement, gross asset test, and anti-abuse provisions under Treasury Regulations, require careful analysis. Non-compliance with these requirements could result in disqualification of the exclusion and significant additional tax liability.

How should we be using multiple trusts to “stack” and “pack” QSBS exclusions for different family members? This technique, when properly implemented, can multiply the available exclusion across generations.

What is our contingency plan if Congress modifies the QSBS rules under IRC Section 1202? The 100 per cent gain exclusion has been subject to ongoing legislative scrutiny, and planning should account for potential future changes to the law, though no structure can be guaranteed to be "reform-proof" against future legislation.

Are our buy-sell agreements, shareholder agreements, operating agreements, and other governance documents aligned with our current estate plan, and do they reflect the current federal estate and gift tax exemption framework established by the OBBBA? Documents drafted during the sunset uncertainty period may need significant revision.

Art, collectibles, and tangible personal property: Valuation, charitable strategies, and asset protection
For collectors of fine art, rare automobiles, wine, jewelry, numismatic items, or other valuable tangible personal property, the estate tax framework creates both planning opportunities and heightened IRS attention to valuation methodologies. The OBBBA’s permanence means that the Service is investing in long-term enforcement infrastructure, and art and collectibles remain prime audit targets.

Questions to ask your advisors
When was our collection last appraised, and do our appraisals meet the requirements for "qualified appraisals" under IRC Section 170 and Treasury Regulation Section 1.170A-13? The IRS Art Advisory Panel reviews returns involving art valued at $50,000 or more, and penalties for substantial valuation misstatements under IRC Sections 6662 and 6663 can range from 20 per cent to 40 per cent of the underpayment, with potential criminal penalties in cases of fraud.

How should we structure charitable remainder trusts under IRC Section 664 or other split-interest charitable gifts involving appreciated collectibles? While the OBBBA preserved the Section 199A Qualified Business Income deduction, practitioners should note that tangible personal property contributed to CRTs may be subject to special valuation rules under IRC Section 170, and the relationship between Section 199A and charitable planning with collectibles should be carefully analyzed with qualified tax counsel.

What is the optimal holding structure for our collection – direct ownership, limited liability company , trust, or a combination thereof? Each approach carries different implications for liability protection, estate tax inclusion under IRC Sections 2031-2046, income tax basis adjustment under IRC Section 1014, gift and estate tax valuation under IRC Sections 2031 and 2512, and operational flexibility. The choice of structure should be made in consultation with legal and tax advisors based on your specific circumstances and objectives.

Are our insurance policies, storage arrangements, and loan agreements properly documented and integrated with our estate plan? Art lending programs, museum loans, and securitized borrowing against collections create planning complexities that require coordination across legal, tax, and risk management professionals.

For families with collections crossing international borders, how do we manage import/export compliance , foreign storage, and multi-jurisdictional ownership without triggering unintended US or foreign tax consequences or reporting failures under the Foreign Account Tax Compliance Act , Report of Foreign Bank and Financial Accounts requirements under 31 USC 5314, Form 3520 , and other international reporting obligations?

Trust modernization: Situs, flexibility, and the erosion of fiduciary duties
The 2026 Heckerling Institute emphasized that trusts are no longer “set it and forget it” vehicles. Geographic fragmentation of families and the shift toward liquid financial assets have unmoored traditional locational anchors. The draft Uniform Conflict of Laws in Trusts and Estates Act, if adopted by states, would provide guidance on multi-state and international trust administration challenges, though as of the date of this article, it remains in draft form and has not been widely enacted.

Simultaneously, states like South Dakota, Delaware, and Tennessee continue expanding Directed Trust and Silent Trust statutes, allowing settlors to significantly reduce a trustee’s duty to monitor or inform beneficiaries. For families holding operating businesses or concentrated collections in trust, these developments create both opportunity and risk.

Questions to ask your advisors
Is our trust situs still optimal, or should we consider migration to a jurisdiction with more favorable tax treatment, asset protection statutes, or perpetuities rules? Trust “situs shopping” remains common practice, but the legal landscape is shifting, and aggressive positioning may invite a challenge.

How do our dynasty trusts maintain flexibility as fiduciary income tax rules and state laws evolve? Today’s ironclad structure could become tomorrow’s straitjacket. Trust protector powers, decanting authority, and modification provisions should be stress-tested against foreseeable changes.

Do our trusts holding family business interests or art collections have appropriate directed trust provisions, and are the roles of investment direction advisors, distribution advisors, and administrative trustees clearly delineated?

For families using spousal lifetime access trusts , what protections exist if the marriage breaks down? With more couples using sophisticated dual-SLAT structures, clearer standards are needed to protect both spouses – and their advisors.

Asset protection: Domestic and foreign structures for high-profile assets
Domestic Asset Protection Trusts are now available in 21 states, and practitioners at Heckerling 2026 provided detailed guidance on structuring these vehicles for families with concentrated business interests or valuable collections. For high-risk clients – those with litigation exposure, professional liability, or simply significant public profiles – Foreign Asset Protection Trusts may offer certain advantages in specific circumstances, though they involve additional compliance requirements including FBAR and Form 3520 reporting obligations.

Questions to ask your advisors
What is our current creditor exposure, and have we stress-tested our existing structures against the most likely litigation scenarios affecting business owners and collectors?

Are Inter Vivos QTIP Trusts preferable to SLATs for our situation? These vehicles can offer superior asset protection in certain jurisdictions while maintaining marital deduction benefits.

For families with international operations or residences, how do we balance asset protection with full compliance with FBAR, FATCA, Form 3520, and other international reporting requirements?

Litigation risk, capacity documentation, and elder financial protection
When estate planning involves tens or hundreds of millions in family business interests and collectibles, every document may eventually be examined in litigation. The Heckerling Institute highlighted that 87.5 per cent of elder financial abuse goes unreported, and many states have enacted statutory remedies including treble damages and mandatory fee-shifting to empower enforcement against exploiters.

For families with aging family members, the intersection of capacity concerns, undue influence allegations, and complex asset structures create heightened risk.

Questions to ask your advisors
How are we documenting capacity and intent for significant planning transactions? Best practices for memorializing family dynamics and decision-making capacity have become essential protective measures.

What protocols exist for identifying and responding to potential financial exploitation? Advisors increasingly face situations where statutory guidance is unclear and families are resistant – yet the ethical and legal duties are real.

Have we “tested the system” of community-based care and family support before a crisis occurs? Planning for incapacity is as important as planning for wealth transfer.

Technology, AI, and cybersecurity: The new fiduciary standard of care
Technological competence under American Bar Association Model Rule 1.1 is now a mandatory ethical requirement for estate planning practitioners. Generative AI tools create both efficiency opportunities and confidentiality risks – sensitive client data fed into unsecure public tools can create ABA Model Rule 1.6 violations. For families with valuable collections, business trade secrets, or simply high public profiles, cybersecurity is not optional.

Questions to ask your advisors
How does your firm vet and document AI use in drafting, analytics, and client communications? Technology can enhance planning, but only within clear fiduciary guardrails.

What cybersecurity protocols protect our sensitive financial, medical, collection inventory, and personal information? Courts are beginning to articulate expectations for fiduciaries holding digital assets and confidential data.

How do our various advisors – legal, tax, investment, family office, insurance, and art consultants – share information efficiently without crossing ethical or confidentiality boundaries?

Retirement account integration: The SECURE Act legacy
For UHNW families, substantial retirement accounts often represent a significant – and highly taxed – component of wealth. The SECURE and SECURE 2.0 Acts created new complexities around required minimum distributions, beneficiary designations, and trust planning for inherited IRAs.

Questions to ask your advisors
Are our retirement account beneficiary designations coordinated with our overall estate plan, and do they reflect post-SECURE Act realities?

What is our Roth conversion strategy, and how does it integrate with charitable planning, trust funding, and business succession timing?

For very large inherited IRAs, what strategies exist for separate accounts, see-through trust provisions, and beneficiary communications to optimize the 10-year distribution window?

Conclusion: Building for precision, not urgency
The estate planning profession has entered what practitioners describe as a post-sunset landscape. The traditional tax-driven urgency that dominated planning for a decade has been replaced by a mandate for high-level technical precision and ethical vigilance. For families with operating businesses, significant art collections, or valuable collectibles, this means that strategies built on assumptions from even five years ago require serious stress-testing.

The complexity of modern families, the transparency of the digital age, and the permanence of the new exemption framework mean that “bad facts make bad law” more often than ever.

Your professional advisors should be as much risk managers as technical planners – and the questions you ask them will determine whether your wealth transfer strategy is built to last.

Matthew Erskine

DISCLAIMER
This article is for general informational purposes only and does not constitute legal, tax, or financial advice. The information provided reflects the author’s observations on current estate planning developments and should not be relied upon as a substitute for consultation with qualified legal, tax, and financial professionals regarding your specific circumstances. Laws and regulations vary by jurisdiction and are subject to change. Readers should consult with their own professional advisors before taking any action based on the information discussed in this article.