Every tax tool, analyzed. 67 and counting.
Deferral, exclusion, offsets, charitable, estate and residency moves, plus the red flags the IRS has listed. Each analysis covers how it works, who it fits, the IRS stance and the catch.
0% capital gains harvesting
Fill the 0% long-term capital gains bracket on purpose each year, by harvesting gains or by spreading a sale with an installment note.
Read the analysisdeferral1031 boot
Cash out, debt not replaced, or a note from the buyer: how boot is taxed in a 1031, how mortgage netting works, and how to spread boot over time.
Read the analysisdeferral1031 exchange
Defer the whole gain by trading investment real estate for more real estate, if you can find it and close inside 180 days.
Read the analysisoffset338(h)(10) election
A stock sale taxed as an asset sale: the buyer's step-up, the seller's extra tax, and the gross-up.
Read the analysisdeferral721 UPREIT exchange
Contribute property (often after a 1031 into a Delaware statutory trust) to a REIT's operating partnership for units: deferral now, step-up at death, but no more 103
Read the analysischaritableBargain sale to charity
Sell property to a charity below market value: part sale, part gift, with basis split between the two and a deduction for the gift part.
Read the analysisRed flagCash-out refinance before a sale
Borrowed money is not income, but a refinance just before a sale does not shrink the gain and can speed up the tax on an installment sale or a 1031.
Read the analysischaritableCharitable gift annuity
A contract with a charity: you give property, the charity pays you a fixed amount for life, and part of the transfer is a deductible gift.
Read the analysischaritableCharitable lead annuity trust
A trust that pays a charity a fixed amount every year, then passes what is left to your family, with a deduction up front or a smaller taxable gift.
Read the analysischaritableCharitable lead trust
Charity gets the payments first, family or you get what is left: how a grantor lead trust can offset a big sale year, and how a non-grantor lead trust moves wealth to hei
Read the analysischaritableCharitable LLC
An ordinary LLC you control and use for giving and impact investing. It is not a charity, so putting money in earns no deduction and defers no gain.
Read the analysisdeferralCharitable remainder trust
Give appreciated property to a trust before the sale, let the trust sell it, take an income stream for life or up to 20 years, and leave the rest to charity.
Read the analysisdeferralContingent payment installment sale
When part of the price depends on future results, Section 453 still spreads the tax, but basis recovery follows special rules.
Read the analysisoffsetCost segregation before a sale
Faster depreciation now, ordinary recapture at sale: when a late cost segregation study still pays.
Read the analysisdeferralDeferred sales trust
A branded installment sale to a third-party trust: how it works under Section 453, what it costs, and where the IRS could attack it.
Read the analysisdeferralDelaware statutory trust
A passive, fractional 1031 replacement property: how Rev. Rul. 2004-86 makes it work, what the sponsor controls, and what it costs.
Read the analysisdeferralDepreciation recapture on an installment sale
Recapture is taxed in year one no matter how the buyer pays; here is how much, why, and the down payment that covers it.
Read the analysischaritableDonor-advised fund (appreciated assets)
Give appreciated stock, real estate or business interests to a donor-advised fund before a sale: no gain to you, a fair market value deduction, grants later.
Read the analysisdeferralDownREIT
Contribute property to a REIT-controlled partnership for units that track REIT dividends, deferring gain under Section 721 until you convert.
Read the analysisdeferralEarn-out
How contingent business sale payments are taxed, and the interest and compensation traps in the drafting.
Read the analysisdeferralElecting out of the installment method
Sometimes paying all the tax up front is cheaper; here is when the 453(d) election out wins and when it backfires.
Read the analysisdeferralESOP Section 1042 rollover
Sell C corporation stock to your employees' ESOP, reinvest in U.S. operating company securities, and defer the gain, possibly for life.
Read the analysisestateEstate tax deferral (6166)
Section 6166 lets an estate built around a closely held business pay its estate tax over as long as 14 years at low interest, so the heirs do not have to sell the busines
Read the analysisdeferralExchange fund
Pool a concentrated stock position into a partnership with other investors to diversify without selling, if you can wait seven years.
Read the analysisdeferralFailed 1031 exchange
Missed day 45 or day 180? The sale becomes taxable, but a little-known regulation can move the gain into the year the intermediary releases the money.
Read the analysisestateFamily limited partnership
A family limited partnership can shift assets to heirs at a valuation discount for gift and estate tax, but it does not defer income tax on a sale and the IRS attacks slo
Read the analysisestateGifting shares before a sale
Giving company shares to family members before a sale can shift part of the gain to lower brackets or lower-tax states, but only if the gift happens before the deal is ef
Read the analysisdeferralImprovement 1031 exchange
Use exchange money to build or renovate the replacement property, with the work finished before it comes to you inside 180 days.
Read the analysisdeferralInstallment sale (Section 453)
Report the gain as the buyer pays you instead of all in the year of sale, under rules that have been in the tax code for decades.
Read the analysisestateInstallment sale to an IDGT
Selling to your own grantor trust for a note is invisible for income tax and can freeze estate value, but it does not defer tax on a real sale.
Read the analysisRed flagMalta pension plan
A treaty play the U.S. and Malta shut down in 2021; the IRS has proposed listing it and audits it as an abusive arrangement.
Read the analysisRed flagMicro-captive insurance
An 831(b) captive that turns business income into deductible premiums; certain versions are listed transactions under 2025 final regulations.
Read the analysisRed flagMonetized installment sale
An intermediary note plus a loan to the seller, marketed as cash now and tax later. The IRS says it does not work and has proposed making it a listed transaction.
Read the analysisresidencyMoving states before a sale
Becoming a resident of a no-income-tax state before you sell can remove state tax on some gains, but only for the right asset, with the right timing and a real move.
Read the analysisdeferralNet unrealized appreciation (NUA)
If your 401(k) holds highly appreciated company stock, the NUA rules can turn ordinary income into long-term capital gain, if you take the right kind of distribution.
Read the analysisresidencyNING / DING trust
Incomplete gift non-grantor trusts were built to move a big gain out of a high-tax state. California and New York now tax them to the grantor, and the IRS stopped issuing
Read the analysisoffsetOil and gas IDC
Drilling cost deductions can offset ordinary income in a sale year, with recapture and real investment risk.
Read the analysisdeferralOpportunity Zones
Original 2017 rules and OZ 2.0 under the One Big Beautiful Bill Act: rolling 5-year deferral, 10% or 30% step-up, 10-year exclusion, and how installment payments feed a f
Read the analysisdeferralOpportunity Zones 2.0
OBBBA's permanent opportunity zones: rolling five-year deferral, rural step-up, and pairing with an installment sale.
Read the analysisexclusionPersonal goodwill sale
Selling the owner's own goodwill directly to avoid the corporate layer of tax, and what makes it fail.
Read the analysischaritablePooled income fund
Give appreciated assets to a charity's shared trust, skip the gain on the transfer, and receive a share of the fund's income for life.
Read the analysisdeferralPrepaid variable forward
Cash now for public stock you deliver later, deferring the sale under Rev. Rul. 2003-7, as long as you avoid share lending and constructive sale traps.
Read the analysisestatePrivate annuity
Swapping property for a family member's promise of lifetime payments once spread the gain; proposed rules since 2006 would tax it up front.
Read the analysisdeferralPrivate placement life insurance
A neutral look at PPLI: it can shelter future investment growth under 7702 and 817(h), but it does nothing for the gain on the sale itself.
Read the analysisresidencyPuerto Rico Act 60
A real exclusion for genuine Puerto Rico residents, but the 10-year rule keeps pre-move gain in U.S. tax and the IRS audits residency claims.
Read the analysisoffsetPurchase price allocation
How the Section 1060 split between goodwill, equipment and non-competes sets the tax on a business sale.
Read the analysisexclusionQSBS (Section 1202 and 1045)
Exclude up to $15 million or 10 times basis of gain on qualified C corporation stock, and roll gain into new QSBS within 60 days under Section 1045.
Read the analysisexclusionQSBS stacking
Gifting qualified small business stock so each taxpayer gets its own Section 1202 cap, and where it fails.
Read the analysisdeferralRelated-party installment sale
You can carry a note for your child or your own company, but three rules can pull the deferred gain into the current year.
Read the analysisdeferralReverse 1031 exchange
Buy the replacement property first and sell the old one later, using a parking arrangement under Rev. Proc. 2000-37.
Read the analysisexclusionRoth conversion in a sale year
Why converting an IRA in a big sale year usually costs more, and when spreading the sale opens cheaper years.
Read the analysisoffsetSale-leaseback
Sell the building your business uses and lease it back: cash out the equity, keep the location, and deduct the rent.
Read the analysisdeferralSection 1033 involuntary conversion
When property is condemned, destroyed or sold under threat of condemnation, Section 1033 defers the gain if you reinvest in time.
Read the analysisexclusionSection 121 plus 1031
A former home that became a rental can use both the home sale exclusion and a 1031 exchange on the same sale under Rev. Proc. 2005-14.
Read the analysisdeferralSection 453A interest charge
Installment notes over $5 million carry a yearly interest charge on the deferred tax; here is the formula, a calculator and the exceptions.
Read the analysisdeferralSection 453A pledge rule
Borrowing against your installment note can trigger the deferred tax early; here is exactly when, how much, and who is exempt.
Read the analysisestateSelf-cancelling installment note (SCIN)
A family installment note that disappears at the seller's death can shrink the estate, but the income tax still comes due and the IRS tests the price.
Read the analysisdeferralSeller financing
Carry the buyer's note, collect interest, and pay the tax as the principal comes in, with the right collateral and terms behind it.
Read the analysisoffsetSolar tax credits
Buying or earning solar credits after OBBBA, and why passive and AMT limits often block them in a sale year.
Read the analysisestateSpecial use valuation (2032A)
Section 2032A lets a family farm or business building be valued at its current use instead of its best price for estate tax, if the heirs keep it in use for ten years.
Read the analysisexclusionStep-up at death (hold)
Holding an appreciated asset until death can erase the built-in gain for heirs; here is when that beats selling now and when it does not.
Read the analysisRed flagSyndicated conservation easement
A listed transaction the IRS treats as abusive: big charitable deductions bought through a land partnership, now curbed by statute and final regulations.
Read the analysisoffsetTax-loss harvesting and the loss bank
Count every loss you already own, capital carryforwards, suspended passive losses and Section 1231 losses, and line them up against the sale gain.
Read the analysisdeferralTenancy in common (TIC) 1031
Exchange into a fractional, undivided deeded interest in a larger property, under the Rev. Proc. 2002-22 guidelines.
Read the analysisdeferralWrap-around mortgage
Keeping your old loan in place under a bigger seller-financed note can cut year-one gain, if the lender and the paperwork cooperate.
Read the analysisdeferralYear-end closing timing
December or January? The closing date picks the tax year, the estimated tax bill, the Medicare premium two years out and which deductions still count.
Read the analysisdeferralZero-cost collar
Buy a put, sell a call, and hold the stock: downside protection without a sale, if the band is wide enough to avoid a 1259 constructive sale.
Read the analysisNot sure which tools fit your sale?
The $5,000 Big Sale Tax Analysis runs the ones that fit side by side and ends with a written recommendation.
Prefer email? Request the analysis by email.