Notes and commentary on federal and state tax matters, real estate tax, partnership and entity-level taxation, and tax controversy practice. Articles are written for sophisticated readers — tax professionals, real estate investors and developers, family offices, and the high-net-worth families their work serves — and reflect the firm’s tax-first approach to real estate practice.
On May 13, 2026 the IRS opened a tiered, time-limited settlement for conservation-easement disputes: concede the charitable deduction for a 10% penalty within 90 days of the letter, 20% within 135 days, or face the 40% penalty and a ~5–7% deduction in litigation after that.
Continue reading →A station-by-station map of the federal tax dispute system. Read in order, or jump to the stage you need.
A map of the entire federal tax dispute system, from the moment a return is filed to the courtroom where it may end. The high-level overview; each station below has its own detailed post and map.
Continue reading →How a filed return becomes a liability: return processing, math-error notices, the underreporter (CP2000) path, and the assessment that starts the ten-year collection clock.
Continue reading →How audits actually run — correspondence, office, and field exams; the information document request; the 30-day letter; and the statutory notice of deficiency that closes an unagreed case.
Continue reading →How to contest an assessment once the normal audit track has closed: audit reconsideration and a doubt-as-to-liability offer when the tax is unpaid, a refund claim when it is paid, and innocent-spouse relief either way.
Continue reading →The IRS Independent Office of Appeals — the hazards-of-litigation settlement standard, how cases enter from exam and collection, and the two very different clocks that lead out to the Tax Court.
Continue reading →The notice stream from CP14 to the final notice of intent to levy, the federal tax lien versus the levy, the Collection Due Process hearing, and the ten-year collection statute that frames it all.
Continue reading →Resolving an unpaid balance, ordered by ability to pay: installment-agreement tiers, partial-pay plans, currently-not-collectible status, offers in compromise, and the lien relief that travels alongside them.
Continue reading →Where a tax case is litigated: the prepayment route to the U.S. Tax Court, the pay-first refund forums of district court and the Court of Federal Claims, and the appellate ladder to the Supreme Court.
Continue reading →The lien and the Notice of the lien are not the same thing. When the IRS files an NFTL and the $10,000 threshold behind it, when filing is discretionary and what the IRS weighs, how to prevent a filing, your CDP rights once it is filed, and the four certificates that remove or move it — release, withdrawal, discharge, and subordination — with the grounds, forms, and timing for each.
Continue reading →A levy is the seizure, not the claim. The sequence of notices that must precede it, the 30-day Final Notice and the CDP request that suspends a levy, what a levy reaches and the property exempt from it, and every way to fight or release one — CDP, economic-hardship release under § 6343, collection alternatives, wrongful-levy claims, and damages.
Continue reading →The great exception to the corporate shield. How § 6672 turns unpaid payroll trust-fund tax into the personal liability of the people who ran the finances — the two-prong responsible-person and willfulness test, the Form 4180 interview, the 60-day Letter 1153 window, the divisible-tax refund route, and how to fight an assessment.
Continue reading →Since the FAST Act, an IRS balance can cost you your passport. What a “seriously delinquent tax debt” is — the 2026 threshold over $66,000 plus a lien-or-levy predicate — what CP508C certification does, the exclusions that prevent it, how a CP508R reversal works, and judicial review under § 7345(e).
Continue reading →The engine of an IRS investigation. The § 7602 power, the three kinds of summons, your notice and 20-day petition-to-quash rights on third-party summonses, John Doe summonses, the Powell enforcement standard, privilege and Fifth Amendment defenses, and the § 7602(d) referral bar.
Continue reading →For international clients, the reporting penalties dwarf the tax. The FBAR under 31 U.S.C. § 5321 (non-willful, willful, and criminal, after Bittner), Form 8938 and the § 6038/§ 6677 information returns, the live Farhy/Mukhi assessability split, and the streamlined and voluntary-disclosure paths back.
Continue reading →Some tax debts are paid; some simply expire. The ten-year collection statute under § 6502, the § 6503 events that toll it, what Currently Not Collectible (Status 53) does and does not do, and why CNC — which does not toll the CSED — can be the cheapest way out of a tax debt.
Continue reading →Title is not protection if control and benefit stay behind. How the IRS follows value into a spouse’s name, an LLC, or a relative’s account — transferee liability under § 6901, nominee liens, and alter-ego veil-piercing — with the badges of fraud and the procedural line between an administrative levy and a suit.
Continue reading →When administrative collection cannot reach the equity, the government sues. Reducing the assessment to a judgment that outlasts the collection statute, foreclosing the lien under § 7403, and United States v. Rodgers — the forced sale of an entire property co-owned by a non-delinquent spouse.
Continue reading →When only one spouse owes, whether the IRS can take the house turns on how the deed reads. The lien and a § 7403 forced sale across sole ownership, tenancy in common, joint tenancy with survivorship, and community property — with tenancy by the entirety treated in a companion post.
Continue reading →Tenancy by the entirety was once a near-complete shield against one spouse’s tax debt. United States v. Craft ended that — but entireties property is still hard for the IRS to take. The full analysis: attachment, the § 7403 forced sale, the valuation split, the court’s discretion, and survivorship.
Continue reading →The emergency exception to ordinary assessment. When the IRS fears the money will vanish, it can assess and levy immediately under § 6851 and § 6861/§ 6862 — with Chief Counsel approval and a fast § 7429 review (5-day statement, 30-day request, a court decision in 20 days).
Continue reading →When you don’t file, the IRS files for you — in the worst-case way. Why a § 6020(b) substitute for return maximizes the tax, never starts the assessment statute, and is generally non-dischargeable in bankruptcy — and why filing your own return is the fix.
Continue reading →The IRS’s most severe civil sanction — the 75% § 6663 fraud penalty — and the most dangerous audit. The clear-and-convincing burden, the badges of fraud, and how a civil exam can be suspended and referred to Criminal Investigation, without warning, the moment firm indications of fraud appear.
Continue reading →Penalties can dwarf the tax. A map of the civil penalties — § 6651, § 6662, § 6663 — and the two defenses that matter most: reasonable cause under § 6664(c), and the § 6751(b) supervisory-approval requirement, where the IRS bears the burden (Chai, Graev, Laidlaw, Kroner, and the new regulations).
Continue reading →Where tax enforcement stops being about money and starts being about liberty. The offenses — evasion (§ 7201), failure to file (§ 7203), false returns (§ 7206), the omnibus clause and Marinello — the willfulness standard of Cheek, how IRS Criminal Investigation builds a case, and the civil-criminal interface.
Continue reading →The letter arrives in a plain envelope from the Internal Revenue Service. The taxpayer’s name and address appear in the upper-left corner. There is a number in the upper right that means something to the IRS but very little to most taxpayers. The first 30 days after that letter arrives matter more than most people realize.
Continue reading →What a written tax opinion contains, the purpose it serves, and how it delivers penalty protection under §§ 6662, 6664 and 6694 — plus the confidence ladder, from frivolous to will, with the standards and the odds commonly attached to each.
Continue reading →What a written tax opinion contains, the purpose it serves, and how it delivers penalty protection under §§ 6662, 6664 and 6694 — plus the confidence ladder, from frivolous to will, with the standards and the odds commonly attached to each.
Continue reading →Tax law looks like ten thousand unrelated rules. It is not. Every tax question resolves into three variables — the character of an item, its amount, and its timing. The single framework that sits underneath all tax planning, with real estate examples on every axis.
Continue reading →Three Code provisions stack to turn a single short-term rental into a six-figure first-year deduction against W-2 income: the seven-day rule of Reg. § 1.469-1T(e)(3)(ii)(A), material participation, and the cost-segregation loss engine — and the one place the play almost always fails.
Continue reading →REPS is not an election and not a title — it is a year-by-year factual test under § 469(c)(7). Two gates met by one spouse alone, the 50% test that disqualifies most W-2 earners, and the separate material-participation step with its § 469(c)(7)(A) aggregation election.
Continue reading →The seven tests of Reg. § 1.469-5T(a), what actually counts as participation under (f) — including the investor-capacity nuance most logs get wrong — and the special rules for limited partners, spouses, and pass-through look-backs.
Continue reading →Section 469(c)(2) makes every rental passive per se — no matter how hard you work. Six independent regulatory exits remove an activity from the “rental” definition, including the seven-day rule, after which ordinary material-participation analysis governs.
Continue reading →Rent a residence for fewer than 15 days a year and the income is excluded entirely — not deferred. Read through the character-amount-timing framework, it is one of the cleanest moves available to a business owner, with a fifteen-day cliff and strict substantiation guardrails.
Continue reading →The two-entity structure separates land-holding from development across two related entities, so the pre-development appreciation runs through one entity as long-term capital gain and the development profit runs through the other as ordinary income. The doctrinal foundation, the § 453(e) trap, the partial-overlap variation, and what kills the structure on audit.
Continue reading →A tax strategy that produces $1,500,000 of first-year deductions sounds spectacular until the taxpayer learns that, of the $1,500,000, only $626,000 will offset other income this year. The remaining $874,000 becomes a net operating loss subject to § 172’s 80% taxable-income limitation. How to model the real benefit, not the headline benefit, post-OBBBA.
Continue reading →Properly structured, the “short-term rental loophole” can convert a real estate investment into a substantial federal tax deduction in the first year of ownership. Improperly structured — which is more common than its enthusiasts acknowledge — it produces nothing but a depreciation schedule that runs forever and a notice from the IRS two years later. The actual mechanics of § 469, the 7-day rule, and the 100-hour test.
Continue reading →When real estate developers and fund sponsors send a partnership agreement to their attorney for review, the attorney typically reads it as a legal document. That review misses something important. The partnership agreement is also — and in a real sense, primarily — the tax framework of the deal. Almost every economic outcome the partners care about is determined by tax provisions buried inside the agreement.
Continue reading →Selling lots out of a subdivision requires equitable apportionment of basis under Reg. § 1.61-6 — and the alternative cost method of Rev. Proc. 92-29 lets a developer pull estimated future common-improvement costs into the basis of lots sold before those costs are spent.
Continue reading →Foreign persons selling U.S. real estate face a federal withholding regime that operates very differently from ordinary income tax. The Foreign Investment in Real Property Tax Act — FIRPTA — requires the buyer (acting as withholding agent) to withhold a percentage of the gross sale price at closing. The mechanics matter, and the consequences of getting them wrong fall on the parties unequally.
Continue reading →Disclaimer. Articles on this page are provided for general informational purposes only and do not constitute legal or tax advice. Readers should not act on any information without consulting qualified counsel familiar with the specific facts and applicable law of their matter. Reading these articles does not create an attorney-client relationship with Donovan Legal PLLC or any of its attorneys. Each tax and legal matter is unique and outcomes depend on specific facts, applicable law, and circumstances.