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Estate Planning

Tax-efficient strategies for transferring wealth and business assets to the next generation

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May 16, 202612 min read

Step Transaction Doctrine: How the IRS Collapses Multi-Step Tax Plans

The step transaction doctrine lets the IRS treat a sequence of formally separate steps as one taxable transaction. This guide explains the three tests courts apply — end result, mutual interdependence, and binding commitment — the landmark cases (Gregory v. Helvering, Court Holding, Kimbell-Diamond), the 2026 transactions most exposed (1031 drop-and-swaps, pre-sale entity conversions, gifts before the estate exemption sunset), and the documentation habits that keep multi-step plans defensible.

Mike Thrift

tax-planningtax-compliancereal-estate

May 15, 202611 min read

Give It Now or Leave It Later? The Basis Trap That Quietly Costs Families Hundreds of Thousands in Capital Gains Tax

Lifetime gifts under IRC Section 1015 carry over the donor's basis, while inheritance under Section 1014 steps it up to fair market value at death — a difference that can shift a family's after-tax outcome by six figures on a single appreciated position under the 2026 $15 million federal exemption.

Mike Thrift

taxtax-planningestate-planning

May 14, 202612 min read

ABLE Accounts in 2026: How Section 529A Lets People With Disabilities Save $19,000 a Year Tax-Free Without Losing SSI or Medicaid

A 2026 guide to ABLE accounts under IRC Section 529A — the new age-46 eligibility cutoff that makes 6 million more Americans (including 1 million veterans) eligible, the $19,000 annual contribution cap, the $100,000 SSI shelter, the unlimited Medicaid shelter, qualified disability expenses, the ABLE to Work multiplier up to $34,650, and how to avoid Medicaid clawback at death.

Mike Thrift

taxtax-planningpersonal-finance

May 14, 202614 min read

ESBT vs QSST: Choosing the Right Trust to Hold S-Corporation Stock

A side-by-side comparison of Electing Small Business Trusts (ESBT) and Qualified Subchapter S Trusts (QSST) under Section 1361, including who pays the tax, the 2-month-and-16-day election window, and a worked example showing a $118,000 annual tax swing between the two structures on $1M of K-1 income.

Mike Thrift

s-corporations-corptrust

May 14, 202612 min read

ESBT vs QSST: How Trusts Can Hold S-Corporation Stock Without Killing the S Election

A trust holding S-corporation stock must qualify as a QSST or ESBT under Section 1361 or the S election terminates retroactively. A QSST taxes pass-through income at the single beneficiary's personal rate; an ESBT permits multiple beneficiaries but traps S-portion income at the 37% top trust rate. The election deadline is two months and sixteen days from the triggering event.

Mike Thrift

s-corporationtrustestate-planning

May 14, 202613 min read

First-Party vs. Third-Party Special Needs Trusts: SSI, Medicaid, and the Payback Rule

How first-party (d)(4)(A) and third-party special needs trusts differ — funding sources, the Medicaid payback rule, sole-benefit constraints, the 2024 ISM food change, and the 2026 ABLE age expansion — for families protecting a disabled beneficiary's SSI and Medicaid eligibility.

Mike Thrift

trustestate-planninglegal

May 14, 202612 min read

First-Party d(4)(A) vs. Third-Party Special Needs Trusts: Protecting SSI, Medicaid, and a Disabled Loved One's Future

A planning guide to first-party (d)(4)(A), third-party, and (d)(4)(C) pooled special needs trusts. Compares the Medicaid payback obligation, the under-65 statutory cutoff, allowable trust disbursements, the 2024 SSA change that removed food from ISM, and how a 2026 ABLE account complements an SNT without replacing it.

Mike Thrift

trustestate-planningfiduciary

May 14, 202613 min read

The U.S. Exit Tax in 2026: How Form 8854 and Section 877A Tax You on the Way Out

Section 877A treats covered expatriates as if they sold every asset the day before leaving the United States. For 2026 the net-tax threshold is $211,000, the net-worth test sits at $2 million, and the gain exclusion is $910,000 — here is how Form 8854 decides whether you pay.

Mike Thrift

taxtax-compliancetax-planning

May 14, 202610 min read

The $2 Million Mistake: Why Gifting Appreciated Stock to Your Kids Can Be Worse Than Doing Nothing

A practical guide to Section 1015 carryover basis versus Section 1014 stepped-up basis, the dual basis trap for depreciated assets, and the 2026 decision framework for whether to gift appreciated property now or hold until death under the permanent $15 million exemption.

Mike Thrift

estate-planningtax-planningcapital-gains

May 14, 202612 min read

The Section 645 Election: How Form 8855 Treats a Qualified Revocable Trust as Part of the Estate

A trustee's guide to the Section 645 election. File Form 8855 to fold a qualified revocable trust into the related estate during the election period and unlock a fiscal year, the charitable set-aside deduction, a two-year exemption from estimated tax payments, and a single combined Form 1041.

Mike Thrift

estate-planningtrustfiduciary

May 14, 202615 min read

Section 7702B Long-Term Care Insurance: Deduct Premiums, Trade Old Policies, and Keep the Estate Intact

Section 7702B defines tax-qualified long-term care insurance — age-indexed premium deductions up to $6,200 per person in 2026, tax-free benefits under the per diem cap, Section 1035 exchanges from old life or annuity contracts, and hybrid life-LTC structures for aging owners and retirees.

Mike Thrift

insurancetax-deductionstax-planning

May 14, 202613 min read

Section 7702B Qualified Long-Term Care Insurance: Age-Indexed Deductions, Hybrid Life-LTC Policies, and Section 1035 Exchanges

Section 7702B sets the federal rules that decide whether a long-term care policy delivers deductible premiums, tax-free benefits, and tax-free 1035 exchanges. This guide breaks down the 2026 age-indexed deduction limits, the $430 per-diem cap, hybrid life-LTC mechanics, and the planning patterns that move trapped cash value into care coverage without recognizing gain.

Mike Thrift

tax-planninginsurancehealth-insurance

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