Behind the Numbers: Real Tax Strategies That Delivered Real Results

Table of Contents

• If you’ve missed the earlier parts of this series, …

• Case Study 1: Unlocked Real Estate Losses – $74K S …

• Case Study 2: Shifting Income, Slashing Taxes, and …

• Case Study 3: Structure Smarter: The Tax and Legal …

• The Bottom Line

Welcome to Part 4 of our 5-part Tax Planning Series.

Today, we're diving into real-life case studies. These are real clients with real challenges, and we’ll walk you through a high-level overview of their situation and how we helped them reduce their tax burden.

Each of these examples comes from our premium Wealth and Tax Optimization program—our high-touch service designed for high-net-worth individuals who need a customized, long-term tax strategy. These aren’t one-and-done tactics. Tax planning doesn't happen in a vacuum. It requires a deep understanding of the full financial picture and often spans multiple years.

Our goal in this program is simple: to help you protect, grow, and transfer your wealth as tax-efficiently as possible.

If you’ve missed the earlier parts of this series, you can catch up here:

Part 1 - Why Tax Planning Isn't Just for the Wealthy (or Tax Season)

 Part 2 -  Smarter Taxes at Every Stage – Part 2: The Tax Planning Lifecycle

 Part 3 - How the Wealthy Use Tax Planning as a Tool for Growth 

Case Study 1: Unlocked Real Estate Losses – $74K Saved in One Year

This client came to us chasing a short-term rental dream—without realizing how much that dream could pay them back. By guiding them through the tax rules, we helped unlock $74,000 in depreciation deductions in just one year.

Here’s the catch: To deduct real estate losses, you typically need to qualify as a Real Estate Professional (REP)—a high bar that requires 750+ hours and over half your working time in real estate. For someone with a full-time job, that’s tough.

But short-term rentals play by different rules. As long as the couple actively managed the property, REP status wasn’t required, and we could apply a cost segregation strategy to accelerate depreciation.

They saved $74K right away—and they’re now planning for even bigger future wins by shifting one spouse’s focus to full-time real estate.

Case Study 2: Shifting Income, Slashing Taxes, and Supercharging a Roth

This client wanted to convert $400K from a traditional IRA to a Roth—great long-term move, but risky short-term tax-wise. With W-2 income, business profits, and capital gains already stacked up, a standard conversion would’ve triggered a six-figure tax bill.

We stepped in and helped shift business income into the next year while pulling expenses into the current year. With this timing strategy, the client reduced taxable income just enough to make the Roth conversion work.

End result? He converted $400K and only paid $15K in taxes—an $85K savings—and now that money will grow tax-free for life.

Case Study 3: Structure Smarter: The Tax and Legal Win That Pays Off Every Year

This husband-and-wife team were doing well—but both were operating as sole proprietors, which meant higher audit risk and thousands in avoidable taxes.

We showed them how restructuring as LLCs taxed as S-Corps could change everything. Why?

• Lower Audit Risk: S-Corps file separate business returns—less red flag than Schedule C.

• Tax Savings: Only salary is hit with payroll taxes; remaining profits avoid 15.3% self-employment tax.

By switching structures and setting reasonable salaries, they saved $55,000 in year one—and will continue saving that amount annually, with added legal protection through the LLC.

The Bottom Line

Each of these wins started the same way: a deep dive into the client’s current situation and goals. From there, we modeled what life looks like with and without a plan, offered clear solutions, and met regularly to keep things moving.

And we’re not done yet.

Coming soon: we’re dropping a video walkthrough of our Tax Planning Course—a powerful resource you can access anytime, designed to help you take control of your tax strategy.

And in Part 5 of this series, we’ll cover a foundational truth: Why Tax Planning Starts with Clean Books.

Because great tax planning isn’t a one-time event—it’s a long-term partnership.

Ready to Get Proactive With Your Tax Plan?

We offer three ways to work with us—choose the level that fits your needs: