Real Estate Planning
Real estate is often the most valuable, and the most tax-burdened, asset on a family's balance sheet. The longer you have owned an appreciated property, the larger the success tax waiting at the moment of sale: federal capital gains, depreciation recapture, the 3.8% net investment income tax, and state tax can combine to consume a meaningful share of proceeds. The good news is that there are several well-defined ways to keep more of that capital working: a 1031 exchange, a Delaware Statutory Trust, a 721/UPREIT contribution, or a 1031 paired with a strategic refinance. The right path depends on your income needs, your appetite for management, and your estate goals. We coordinate the choice across the rest of the plan.
What Goes Into Real Estate Investing
Real estate investing involves far more than finding a property and collecting rent. Successful investors evaluate markets, analyze cap rates, project cash flows, arrange financing, manage tenants, and navigate a complex web of tax rules. Each of these elements can make or break the investment.
Location is the foundation: population growth, job creation, landlord-tenant laws, and property-tax rates all vary dramatically from one market to the next. Getting the macro picture right matters as much as choosing the right property.
Then there are the operational details: insurance coverage, maintenance reserves, property management, and lease structures. Real estate rewards those who treat it as a business, not a side hobby.
Four Ways We Help With Real Estate
Right-size the allocation
We help you decide how much of your portfolio belongs in real estate, weighing income and diversification against liquidity and concentration risk.
Pressure-test the deal
We analyze specific deals alongside you, stress-testing assumptions on rent growth, vacancy, and cap-rate compression before capital goes in.
Coordinate the tax strategy
Depreciation, 1031 exchanges, cost segregation, and qualified opportunity zones each carry rules and deadlines. We coordinate with your CPA so every available benefit gets captured.
Integrate with the whole plan
Estate documents, insurance coverage, and retirement projections all need to reflect the property you own. We make sure they do.
Ready to Talk Real Estate?
Whether you own a single rental property or an entire portfolio, we can help you make smarter decisions about acquisition, management, tax planning, and eventual disposition. Our goal is to make sure your real estate holdings strengthen your financial plan rather than complicate it.
We work with investors at every stage: first-time buyers evaluating their first deal, seasoned landlords optimizing an existing portfolio, and business owners considering whether to own or lease their commercial space.
If real estate is part of your financial picture, or you want it to be, let us help you build a plan that accounts for every dimension.
When the Conversation Gets Bigger Than the Property
The Success Tax, and Four Ways Around It
For families holding low-basis property, the most consequential real estate decision is not the buy or the hold; it is the exit. Start with the full comparison of all four paths, then go deeper on the two structures families ask about most.
Start Here · The Overview
Four Paths for Appreciated Property
A side-by-side comparison of all four exits, Sell, 1031, 721/UPREIT, and 1031 + Refinance, run on one worked $5M example so the tradeoffs are visible in numbers.
Compare the four pathsGo Deeper on Two of Them
Explainer
The 721/UPREIT, Explained
A plain-language walk-through of how a 721 contribution actually works: deferring tax, stepping out of active management, and positioning OP Units for a step-up at death.
Comparison
1031 Exchange vs. DST
How the two compare head to head: who each one fits, the tradeoffs between control and passivity, and ten common mistakes to avoid.
A 1031 exchange is a tax event deferred, not a tax event avoided. Treat it like the long-dated decision it is.
Book a conversation to discuss how real estate fits into your overall financial plan.
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