01 · Your Situation
Selling appreciated real estate
Resources
Most investors know real estate has tax advantages. Fewer understand how depreciation, gain deferral, loss utilization, and holding-period strategy work together. These guides explain the rules, the mechanics, the math, and when each strategy is most useful.
New here? Start with the pillar guide, then move to 1031 exchanges, cost segregation, REPS, or opportunity zones based on your situation.
Start Here
01 · Your Situation
Selling appreciated real estate
02 · Your Situation
High-income W-2 earner
03 · Your Situation
Sitting on a large capital gain
04 · Your Situation
Looking for a passive 1031 exit
Core Guides
Everything in tax-advantaged real estate investing flows from a small set of core concepts: depreciation, accelerated depreciation, gain deferral, loss utilization, and holding-period strategy. Start with these guides to understand the full system before moving to the deeper comparisons and deal-specific pages.
The complete overview of real estate tax benefits — depreciation, cost segregation, bonus depreciation, passive loss rules, REPS, and the QBI deduction. Start here if you want the full picture.
Defer capital gains indefinitely using a 1031 exchange. Covers the 45-day / 180-day rules, "swap till you drop," Delaware Statutory Trusts, and the step-up in basis at death.
How opportunity zones eliminate capital gains after a 10-year hold. Covers QOF basics, the 2026 deadline, the 10-year rule, and how OZs compare to 1031 exchanges.
Reclassify building components into shorter depreciation schedules and create large paper losses in year one. Includes real dollar examples for properties at different price points.
MHC Guides
One of America's most structurally advantaged real estate asset classes — supply-constrained, low-turnover, and meaningfully tax-advantaged. Start with the pillar guide and dive deeper from there.
The core guide to MHC investing: economics, operations, tax advantages, return profile, and how to evaluate a deal.
Read Guide →See how NOI growth, leverage, cap-rate movement, and tax benefits combine to drive MHC returns, with worked examples.
Read Guide →Infrastructure liabilities, regulatory risk, rent control, operator risk, and how experienced sponsors mitigate them.
Read Guide →Side-by-side comparison of operating expense ratios, turnover, supply, tax, and return profiles.
Read Guide →Zoning, municipal opposition, and economics make new MHC development nearly impossible — and what that means for existing owners.
Read Guide →Calculators
Use these calculators to estimate tax impact before reading the deeper guides — or to sanity-check a deal you're evaluating.
Estimate your capital gains tax bill and the compounding advantage of a 1031 exchange.
Estimate year-one depreciation, tax savings, and study ROI by asset class.
Calculate year-one deduction and tax savings on short-life property at 100% bonus depreciation.
Compare paying capital gains tax now vs. investing in a QOF for 10+ years.
Further Reading
Side-by-side comparison of both strategies — eligible gains, deferral mechanics, exit taxes, and exactly when to use each.
Compare Strategies →How DSTs work as 1031 exchange replacements — passive income, institutional assets, the seven deadly sins, and how to evaluate one.
Read Guide →How QOFs work, the 90% asset test, self-certifying vs. managed funds, and what to analyze before committing capital.
Read Guide →MHCs have one of the most favorable bonus depreciation profiles in real estate. Infrastructure-heavy composition, 100% permanent bonus depreciation, and real dollar examples.
Read Guide →Now permanently at 100% under current law — the mechanics, what qualifies, and when to use it strategically.
Read Guide →The three income buckets, the $25,000 active participation allowance, and how real estate professional status (REPS) unlocks unlimited deductions against W-2 and business income.
Read Guide →The IRS test that turns paper losses into real deductions against ordinary income — legally.
Read Guide →How IRC §1014 resets tax basis at death — erasing accumulated capital gains and depreciation recapture. Covers the community property double step-up, carryover basis on lifetime gifts, and "swap till you drop."
Read Guide →Side-by-side: one defers gains during life, the other eliminates them at death. Why they work better together, when to use each, and the edge cases that break the strategy.
Compare Strategies →The 20% pass-through deduction — now permanent under OBBBA. The 250-hour safe harbor, 2026 thresholds, W-2 / UBIA limitations, triple-net exclusions, and how QBI stacks with depreciation and REPS.
Read Guide →Popular Topics
Most investors arrive with a specific tax problem to solve. Jump straight to the guides that apply:
Reduce Ordinary Income
Defer or Eliminate Gains
Accelerate Deductions
Put It to Work
Education is step one. Implementation is step two.
These strategies matter most when they are applied thoughtfully in real deals. See how Dayan Capital approaches tax-aware investing for accredited investors.
Important Disclosures
Informational Only
This material is for informational purposes only and does not constitute an offer to sell or a solicitation of an offer to buy any security.
Risk Statement
Investments involve significant risk, including potential loss of principal, illiquidity, long hold periods, use of leverage, and sponsor discretion. Potential conflicts of interest may exist. All projected returns, including target ROI and preferred return figures, are forward-looking statements and are not guaranteed. Actual results may differ materially. Past performance of the MHC sector or any prior investment is not indicative of future results.
Tax Disclaimer
Tax benefits described herein are estimates only; individual tax treatment varies. Consult a qualified financial, legal, and tax advisor before investing.
Offering Documents
Any investment opportunity will be made available only through formal offering documents.
Accredited Investors Only
Investments are available to accredited investors only as defined under SEC Regulation D.
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