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Y1 · Foundation
Building Wealth / Tax strategyCommercial and boring · Year 17 · Deep dive

1031 chains and the step-up in basis

The mechanism the whole roadmap has been walking toward.

1 min

Everything on this site — the boring first deal, the refinance cadence, the move to commercial — has been walking toward one mechanism, and it fits in a sentence: defer the gain for twenty years, then never pay it.

The chain

A 1031 exchange lets you sell a property and roll the entire gain into the next one, untaxed, as long as you follow the deadlines (45 days to identify, 180 to close) and never touch the cash. Do this repeatedly — duplex into fourplex into small multifamily into triple-net — and the deferred gain rides along, growing, never taxed.

The step-up

Deferred is not forgiven — until it is. At death, your heirs receive the portfolio at its stepped-up basis: its market value on that day. The decades of deferred gain don't get taxed later. They stop existing.

This is not a loophole in the pejorative sense. It is written policy, it has survived every tax reform for a century, and it is the single largest difference between the flip road and the hold road at Year 20.

Why this is filed at Year 17

Because by then the chain has links. The planning that matters — entity structure, which assets to chain and which to let go, walking your heirs through what they will hold — is Years 17 through 20 work. The glossary entry on what "tax-free" actually means covers the difference between deferred, sheltered, and never-taxed.