Industries · Real estate

Where the tax code actually rewards getting the details right

Depreciation, passive activity rules, material participation and like-kind exchanges. Real estate has more genuinely valuable tax planning available than almost any other asset class, and more ways to forfeit it by filing on autopilot.

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Three rules that decide most of the outcome

Get these right and the rest is bookkeeping.

One

Passive losses are trapped unless you qualify out

Rental activity is passive by default under Section 469. Passive losses generally cannot offset wages or business income, so a paper loss you were counting on may simply suspend until you sell.

Two

Real estate professional status is a facts test, not a title

Qualifying requires more than half your personal services in real property trades or businesses and more than 750 hours, plus material participation in the rentals. Contemporaneous time records are what wins or loses this in examination, and reconstructed logs routinely fail.

Three

Depreciation is where the money is, and where it comes back

Cost segregation with bonus depreciation can pull large deductions forward. On sale, depreciation recapture is taxed at a different rate than capital gain.

Can this rental loss offset my W-2 income?The order the questions actually get asked in. Every branch is fact-dependent.
1
Is the average period of customer use seven days or less?If yes, it is not a rental activity under the passive loss regulations. It is evaluated as a trade or business, and the question becomes material participation. This is the short-term rental route.
2
Do you qualify as a real estate professional?More than half your personal services in real property trades or businesses, and more than 750 hours. Contemporaneous time records decide this, not job title.
3
Do you materially participate in the activity?Even with real estate professional status, participation is tested activity by activity unless a grouping election is in place.
4
If none of the above applyThe loss is passive. It offsets passive income only, and otherwise suspends until you dispose of the property in a fully taxable transaction. A special allowance of up to $25,000 may apply for active participants, phasing out at higher income.
Most of the money in real estate tax planning is decided in step 1 and step 2. Both are won or lost on records kept as the year happens, which is why reconstructed time logs routinely fail in examination.

What we handle

Investors, short-term rental operators, agents and small developers.

Entity structure

How to hold property across LLCs, when separate entities are worth the administrative cost, and how the structure interacts with financing, liability and your eventual exit.

Cost segregation and depreciation

Whether a study is worth commissioning on a given property, how bonus depreciation applies in the current phase-down, and modeling the recapture consequence before you rely on the deduction.

Short-term rental analysis

Where average guest stay is seven days or less, the activity is not automatically a rental under the passive loss rules, which changes the participation analysis entirely. It also raises occupancy and sales tax questions in Florida.

Section 1031 exchanges

Coordination with your qualified intermediary on the 45-day identification and 180-day closing deadlines, and the basis and depreciation consequences that follow you into the replacement property.

Agent and broker taxation

Commission income is self-employment income. Entity structure, S corp timing, reasonable compensation and quarterly estimates on income that arrives in unpredictable lumps.

Property-level books

Financials per property and in the aggregate, with the basis schedules and improvement records that determine your gain on sale years from now.

The stack

Property-level books, connected end to end

Connected properly, so your books close on live data instead of month-old statements. Where we hold a certification, we say so.

QuickBooks OnlineLedgerProAdvisor
RampCard spendPartner
Bill.comPayablesCertified
GustoPayrollPartner
StripePayments
SquarePayments
BrexCard spend
ExpensifyExpenses
Worth knowing

What costs real estate investors money

  • No contemporaneous time log. Material participation and real estate professional status are won or lost on records kept as you go.
  • Repairs and improvements booked interchangeably. The tangible property regulations distinguish a deductible repair from a capitalized improvement.
  • Cost segregation without modeling the recapture. Accelerating depreciation on a property you intend to sell in three years can convert a modest current benefit into a larger tax bill at a higher rate.
  • A 1031 deadline missed by days. The 45-day identification and 180-day closing periods are strict and are not extended for a deal falling through.
  • Suspended losses forgotten at sale. Passive losses suspended over years generally free up on a fully taxable disposition.
  • Florida tangible personal property tax ignored. Florida has no personal income tax, which is why many investors are here.

General information, not advice for your situation. Outcomes depend on facts we would need to review with you.

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Common questions

Can my rental losses offset my W-2 income?

Usually not, without qualifying for an exception. Rental activity is passive by default and passive losses are generally limited to passive income. There is a special allowance of up to $25,000 for active participants that phases out at higher modified adjusted gross income. Real estate professional status is the main route out for higher earners, and it is a demanding test. Short-term rentals sit in a different category because an average stay of seven days or less means the activity is not treated as a rental for these purposes at all.

Is a cost segregation study worth it?

It depends on the property basis, your marginal rate, whether you can actually use the resulting loss given the passive activity rules, and how long you intend to hold. A study that generates a large suspended passive loss you cannot use for eight years is a much smaller win than the sales pitch suggests. We model it before recommending it.

How does the short-term rental strategy actually work?

If the average period of customer use is seven days or less, the activity is excluded from the definition of a rental activity under the passive loss regulations. That means it is evaluated as a trade or business, and if you materially participate, losses may be non-passive. Material participation still has to be met and documented. It is a legitimate position that is frequently claimed without the participation actually being there.

I am a real estate agent. Should I be an S corp?

Often yes once commission income is consistent, because it can reduce self-employment tax on the distribution portion. It requires real payroll and a defensible salary. Commission income is lumpy, so we also look at whether your quarterly estimates are being calculated properly rather than copied from a year that looked nothing like this one.

Do you work with out-of-state investors who own Florida property?

Yes, and the reverse as well. Florida has no personal income tax, so many of our clients have no state filing here, but property in other states generally creates a filing obligation there.

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