The Strategy Playbook
The moves that actually move the number.
This is a working list of the strategies I use most for high-income owners and real estate investors, with the part of the code behind each one. None of it is exotic and none of it is a loophole someone made up online. It is the mainstream planning that big firms run for wealthy clients, organized so you can see what fits you. Figures are illustrative and depend on your facts. Talk to a CPA before acting.
Part 1 · For Owners & High Earners
Get the structure right first.
Structure is the foundation. The wrong entity or a missed election quietly costs five figures a year. These are the moves that pay for themselves fastest.
Pay yourself a reasonable W2 salary and take the rest of the profit as a distribution that escapes the 15.3% self-employment tax. The highest-ROI move for most profitable owners once profit clears roughly $60k to $80k.
A Solo 401k lets an owner sock away up to $72k in 2026, employee plus employer, all pre-tax. Pair the salary you set for the S-Corp with the plan so the contribution math works in your favor.
For high earners who have maxed the 401k and want to shelter far more, a cash balance pension plan can allow six-figure deductible contributions, scaled to your age and income.
The 20% pass-through deduction phases out above $201,775 single and $403,500 joint in 2026, and faster for service businesses. Retirement contributions, comp, and entity choices can keep you inside the threshold.
A health reimbursement arrangement or a maxed HSA, $8,750 family in 2026, turns medical costs you were paying anyway into deductible business expenses.
Rent your personal home to your own company for up to 14 days a year for legitimate meetings. The business deducts it and you receive the income tax-free. Documentation matters.
Pay your kids a reasonable wage for real work. They use their own standard deduction, the business gets the deduction, and in a sole prop or partnership of parents their wages can avoid FICA.
Bunch several years of giving into one year through a donor-advised fund to clear the standard deduction, and donate appreciated stock to skip the capital gain entirely.
Qualified small business stock can let founders and early employees exclude millions in gain. The holding period and entity type are everything, so this has to be planned years ahead.
Part 2 · For Real Estate Investors
The most tax-favored asset there is.
Real estate is where the code is most generous. The trick is stacking the strategies so a profitable property produces a paper loss that shelters your other income, then deferring the gain when you sell.
Break the building into components and immediately expense the short-life pieces at 100% bonus, now permanent for property placed in service after January 19, 2025. A big year-one deduction on a property that is cash-flow positive.
Qualify as a real estate professional and your rental losses stop being passive. That depreciation can then offset your W2 or business income, not just rental income. The hours tests are strict and must be documented.
A short-term rental with an average stay of seven days or less is not automatically passive. Materially participate and the loss can shelter active income, no REPS required. The favorite move for W2 high earners.
Roll the gain from one property into the next and defer the tax indefinitely. Strict 45-day and 180-day timelines and a qualified intermediary are required, so it has to be set up before you close.
Live in a home two of the last five years and exclude up to $250k of gain single, $500k joint. House hackers and live-in flippers can repeat this over time with planning.
For syndications and multi-owner deals, a §754 election can step up basis for incoming partners and unlock fresh depreciation. Allocations and waterfalls decide who actually gets the tax benefit.
How a Plan Comes Together
Strategy is stacking, not a single trick.
Any one of these helps. The real wins come from combining them in the right order for your situation. Here is the rough sequence I work through.
Project the year
Model your income, business, and real estate before December 31, while every lever is still live.
Fix the structure
Entity, S-Corp election, reasonable comp, and retirement plans set the foundation everything else sits on.
Stack the deductions
Depreciation, QBI, charitable, and family strategies layered in the order that gives the biggest legal result.
Execute & file
Quarterly estimates, clean documentation, and a return that locks in everything we planned. No April surprise.
Which of these fit you?
Let's find out.
Tell me your income, business, and real estate, and I will tell you the first three moves I would make for you specifically.
Book a Free Strategy Call