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The Borrelli Report · Investment Property

Real estate retirement insights.

Answered plainly: the questions owners most often ask when they are exchanging, selling, or weighing what else to do with investment property.

Investment property

1031 exchanges & involuntary conversions

Two sections of the code, two sets of deadlines — and what a sale costs when neither one applies.

New — Interactive

Same exchange. Fifty different states.

The federal clock is identical everywhere. What differs is whether the closing agent holds back your proceeds, whether the state expects a filing every year for as long as you own the replacement, and whether it comes back for the gain when you finally sell. Tap your state.

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New — Interactive

Which states do I have to file in?

The published filing thresholds are for people who work in a state. Income from property, or from a partnership that owns it, is judged by a stricter rule — and one 721 exchange can turn one state return into a dozen. Tick your states and get the question set your CPA would otherwise bill you to build.

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Free tool — 2 minutes

What would selling actually cost?

Capital gain, depreciation recapture and the 3.8% surtax, on your own five numbers. Most owners are working from a rough estimate, and rough estimates in this area tend to be off by a lot in one direction or the other.

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Real Estate · Exit Planning

Done being a landlord? You have five exits — not two.

Keep and delegate, exchange easier, exchange passive, sell and pay, or hold for the step-up — the honest menu, what each path costs, and why only one of them guarantees a tax bill.

Real Estate · 1031 Exchange

Boot: the part of your 1031 that stays taxable.

Keep $300,000 out of a $1,000,000 sale and the exchange survives — but that slice is taxed now. Cash boot vs. mortgage boot, the worked numbers, and the one-way netting rule that catches sellers at tax time.

Real Estate · 1031 Exchange

The reverse 1031: buy first, sell second.

Found the right replacement before you’ve listed? The parking arrangement that makes it legal, the 180-day hard stop, the financing catch — and when a well-planned forward exchange beats it.

Real Estate · Selling

The installment sale: spread the tax, carry the paper.

Take the money over years and the gain follows the payments — except for the depreciation the code pulls into year one. What the down payment decides, and what you take on as the lender.

Real Estate · Charitable

The charitable remainder trust: sell it without the tax bill.

The trust sells free of capital gains tax at that moment and pays you for life. What the payments are actually taxed as, why a mortgage usually ends it, and what your heirs give up.

Real Estate · 1031 Exchange

First 1031 exchange? Start with what it defers — and what it doesn’t.

What a 1031 exchange defers — capital gains tax, depreciation recapture, the 3.8% surtax, and state tax on top — plus the four requirements and a side-by-side of the same property sold two ways.

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Real Estate · 1031 Exchange

How to fill out a 1031 45-day identification form.

The three identification rules, the two unforgiving deadlines, what makes a notice valid — and a free fillable template.

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Real Estate · Section 1033

You lost the property. The IRS may still call it a gain.

Eminent domain, fire, flood: the settlement is measured against your depreciated basis, not what the property was worth. Section 1033, the clocks, and the refund window.

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Selling or exchanging a property this year?

A short briefing on the 45-day and 180-day clocks, what qualifies as replacement property, and the debt requirement most sellers miss. Free.

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