High-Income? It’s Time to Think Beyond April—Start Before December

If your income sits above $500,000—or even hits the $1 million mark—you’re not simply filing taxes. You’re managing a dynamic tax portfolio, and timing is everything. The truth is, most of the most effective strategies to reduce your tax liability require implementation before December 31—not when your CPA is scrambling in March or April.

Year-end planning can drive six-figure differences in tax owed. Why? Because by Q1, many levers—entity restructuring, real estate elections, retirement deferrals, or QBI optimization—are no longer available. That’s why our smartest clients begin their planning in Q3 and Q4.

At Lakeline Tax, we don’t just file returns—we quarterback a proactive strategy that stretches years into the future.

What Keeps Bill Up at Night?

Meet “Big Beautiful Bill”: He’s not just successful—he’s complex. He’s the Austin entrepreneur juggling:

• $1.1M in income from two businesses

• Rental property in Round Rock and Montana

• Crypto assets on three platforms

• Foreign stocks and offshore investments

• Partnerships producing inconsistent K-1s

As Q4 approaches, his questions aren’t just about deductions:

• “Am I paying too much in estimated taxes?”

• “Why did I lose my QBI deduction again?”

• “What if I get audited—will I be ready?”

• “Are my CPA and I playing defense instead of offense?”

These questions stem from something deeper: tax fatigue and complexity paralysis.

Bill needs clarity, strategy, and peace of mind.

The IRS: Friend, Enemy, or Frenemy?

Let’s be honest. For high-income earners, the IRS can feel like all three:

• Enemy: when audits arrive or deductions are denied.

• Mystery: when new tax rules silently disqualify credits and deductions.

• Nuisance: when letters arrive for errors triggered by 1099 mismatches or crypto misreporting.

But with the right planning, the IRS becomes a compliant partner in your wealth strategy.

Here’s how:

• Using IRS-approved grouping rules to unlock rental losses

• Filing amended returns for missed crypto losses or depreciation

• Rescuing QBI with carefully structured W-2 compensation

• Negotiating IRS resolutions with a team of ex-IRS agents on your side

At Lakeline Tax, we specialize in turning the IRS into a manageable, predictable entity—not a wildcard.

Why HNW Clients Are Taxed Into Confusion

The tax code isn’t built for simplicity—it’s built for compliance and complexity. High-net-worth clients are often penalized not because they’re dishonest—but because they’re unaware of the advanced moves available.

Let’s look at Bill’s complexity stack:

• Real estate: Multiple rentals across states, unclear on whether to elect Real Estate Professional Status (REPS), unsure how to use passive losses

• Crypto: Over 200 transactions, spread across wallets and exchanges, with staking rewards, capital gains, and no consolidated 1099

• Foreign holdings: Dividend-generating stocks abroad, triggering FBAR and FATCA filing obligations

• K-1s and partnerships: Passive vs active income not properly grouped; losses that don’t unlock because of poor basis tracking

• Business income: S-Corp salary not properly calibrated, QBI disqualified two years in a row, no retirement planning via defined benefit plans

These aren’t “problems” as much as they are tax planning puzzles—and Lakeline Tax is your expert-level puzzle master.

Lakeline Tax Services That Slash Tax Bills

We aren’t a big-box firm, and we don’t do cookie-cutter returns. We specialize in surgical tax strategy for clients like Bill.

Here’s how:

Tax Planning (Year-Round)

We meet quarterly to assess estimated tax liability, run projections, model income strategies, and assess triggering events before they become problems.

QBI Rescue

Many High income Business owners have lost the Qualified Business Income deduction due to high AGI. We build tax strategies that legally restore this deduction.

Audit Defense

Whether you received a CP2000, notices or letters, a Schedule C inquiry, or a full-blown audit request, we provide expert-level representation, powered by decades of experience—including Enrolled agents with over 20 years of experience.

Entity Structuring & Restructuring

Your LLC from 2019 may no longer be serving your goals. We assess your business activities, income tiers, W-2 vs K-1 dynamics, and future planning needs to implement tax-smart entity maps.

Want to See These Strategies in Action?

Read our full case studies and download your checklist: Tax Planning Checklist & FAQs

Or better yet—schedule a 15-minute Zoom consult with our team:
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Serving Austin, Cedar Park, Leander, Round Rock—and smart HNWIs across the country.

Because tax strategy shouldn’t be seasonal. It should be strategic.