Strategy, markets & tax-deferral thinking.
Clear, practical perspective on 1031 exchanges, DSTs, and building durable real estate wealth — written for owners and investors, not specialists.
1031 Exchange vs. DST: which is right for you?
Both defer capital gains tax — but only one keeps you in the landlord's chair. A practical guide to choosing between an active replacement property and a passive Delaware Statutory Trust.
He wanted his attorney of fifteen years to hold the money. That is the problem
The people you trust most with a transaction are frequently the ones the rules will not let near the proceeds, and the test reaches back two years.
The boot was small. The penalty for not expecting it was not
A partially taxable exchange creates tax in the year of the sale, and the system expects you to have paid most of it long before the return is prepared.
The hail came on day 103, three weeks before closing
A casualty between contract and closing is a contract problem, an insurance problem and a deadline problem at once, and the exchange is the only one of the three that cannot wait.
The loan was approved on day 55. On day 140 they asked for a new entity
A lender who has not done an exchange before can be perfectly willing and still break it, because the borrower, the title and the taxpayer all have to be the same thing.
Three years is the wrong answer to how long you keep the file
A deferral can run for decades, and the basis in your current building depends on paperwork from the one you sold in 1998. The ordinary retention rule does not reach that far.
You sold two buildings six weeks apart. That may be one exchange or two
Where several properties go into a single exchange, the clock starts at the first closing. Treat them as one when they are two, or the reverse, and the dates stop working.
Thirty years of improvements, and nobody kept the receipts
Basis decides your gain, and in an exchange it carries forward into the next property. Undocumented improvements are not a filing inconvenience, they are money.
The warehouse has been in the S corp since 1998. Getting it out is the problem
An S corporation can complete an exchange perfectly well. What it cannot easily do is hand the property to its shareholders, which removes every option partnerships rely on.
Two different things are called a DST, and only one of them is what we mean
A Delaware Statutory Trust is a statutory route into replacement property. A Deferred Sales Trust is a promoted structure. Three shared letters, entirely different footing.
The building is worth less than the loan, and you still owe tax on it
Depreciation can drive your basis far below the debt. Sell at a loss in economic terms and you can still report a gain, with forgiven debt taxed separately on top.
The neighbor was right. Fourteen feet of your parking lot is his
A title commitment tells you what is recorded. Only a survey tells you where it actually sits, and without one your title policy quietly excludes everything a survey would have found.
Eleven years left on the lease. The bankruptcy code says one
When a tenant files, the remaining term stops being a contract and becomes a claim. What that claim is worth is set by statute, and it is a fraction of what the lease says.
The lawsuit arrived before the first rent check. It was about the parking lot
Accessibility claims target current conditions, not who created them. Buy a retail center with a noncompliant ramp and the claim is yours from the day title transfers.
No binder, no loan, no closing. The insurance quote that nearly killed an exchange
Your lender will not fund without proof of insurance, and in some markets carriers are simply not writing. The 180-day clock does not pause while you look for one.
What will selling really cost you in taxes?
Use our free calculator to estimate capital gains, depreciation recapture, and NIIT, then see what an exchange could defer.
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Occasional, substantive notes on tax-deferral strategy and replacement-property trends. No noise.