Tax strategy
Depreciation, cost segregation, 1031 chains and the step-up in basis — shelter while you hold, defer when you trade, step up when you transfer.
12 pieces, ordered by horizon
Y2What "tax-free" actually means on a returnDeferred, sheltered, and never-taxed are three different things.Glossary3mY6The short-term rental tax loophole: sheltering W-2 income without REPSSeven-day average stays plus material participation make STR losses non-passive — no Real Estate Professional Status required. How high earners pair one Airbnb with a cost seg to cut six-figure tax bills, and the hour rules that hold it together.Deep dive6mY10Real Estate Professional Status (REPS): unlocking rental losses against ordinary income750 hours, more than half your working time, and material participation — the tax status that turns paper losses into real refunds, who actually qualifies, and the hour log that wins or loses the audit.Deep dive7mY10Solo 401(k) vs. self-directed IRA for real estate: the retirement-account playbookBoth let retirement money buy property and notes; only one dodges UDFI tax on leveraged deals. The comparison, the prohibited-transaction electric fence, checkbook control, and which assets belong inside at all.Deep dive7mY12Opportunity Zone investing: deferral now, tax-free growth after ten yearsRoll any capital gain into a Qualified Opportunity Fund and the appreciation exits federally tax-free after a decade. The mechanics, the substantial-improvement test, the OZ-plus-cost-seg stack, and who should actually bother.Deep dive7mY12Real estate tax strategy: the complete map of the wealth multiplierDepreciation, cost seg, REPS, the STR loophole, 1031s, Opportunity Zones, entity design, retirement accounts, trusts, and buy-borrow-die — every family of real estate tax strategy, what each is worth, and which ones the IRS is watching.Roadmap12mY12Rental property depreciation and cost segregation: the paper losses that shelter real incomeHow depreciation turns cashflowing rentals into tax losses, how cost segregation accelerates it, bonus depreciation, recapture — and who actually gets to use the losses.Deep dive6mY13Installment sales: spreading the gain, managing the bracket, earning the interestCarry the financing when you sell and the tax spreads across the payment years — bracket management, interest income, and a smoother exit than any lump sum. The rules, the recapture exception, and where the strategy earns its place.Deep dive7mY141031 exchange rules: the complete guide to deferring taxes foreverThe 45-day and 180-day clocks, like-kind rules, boot, qualified intermediaries, and the chain-to-step-up endgame — everything the mechanism requires, in order.Roadmap7mY15Delaware Statutory Trusts: the 1031 landing strip for tired landlordsDSTs let appreciated rental equity exchange tax-deferred into passive fractional ownership of institutional real estate. How they work, the seven deadly restrictions, fee reality, and the exit ramps — 1031 again, 721, or hold to the step-up.Deep dive6mY15Domicile and residency planning: moving before the exit, done properlyWhere you live when you realize a gain can swing the tax by double digits — the domicile checklist auditors actually run, the state rules that follow sellers, Puerto Rico's Act 60, and the timing that makes it all real.Deep dive7mY171031 chains and the step-up in basisThe mechanism the whole roadmap has been walking toward.Deep dive3mMore in Wealth
Raising capital & syndicationFrom partnerships to your first LP raise: securities rules, waterfalls, investor reporting, and reputation as the asset.Large multifamilyApartment communities bought on cap rate and operated by teams — where scale starts working for you instead of on you.CommercialOffice, retail, industrial and triple-net: trading tenant turnover for lease term, and underwriting credit instead of carpets.Portfolio architectureEntities, debt structure at scale, insurance and asset protection — engineering the machine so no single failure reaches the whole.Legacy & transferEstate structure, heirs who understand the machine, and deciding what never gets sold. The point of the whole sequence.