Tax Strategy Blog
Actionable strategies for real estate investors, business owners, and high earners — written by the Roadmap Tax team.
When Your RSUs Vest, Your 10b5-1 Plan Decides the Tax Bill
Your 10b5-1 plan schedules RSU sales but ignores cost basis, AMT timing, and wash sale risks. Each one changes what you owe. Here is how to fix the gaps before tax season.
Your RSUs Are the Biggest Bet You Didn't Choose
Most of your net worth in one stock? How a multi-year plan to diversify RSUs without a tax catastrophe. Walkthrough for tech executives.
Augusta Rule Documentation: 3 Steps to Tax-Free Rent in 2026
The 5 documents you need to survive an Augusta Rule audit: meeting minutes, fair rental comps, payment records, and more. Complete checklist for business owners.
Defined Benefit Plan for Business Owners: 2025 Tax Strategy
Learn how a defined benefit plan helps business owners maximize 2025 tax deductions. Compare cash balance plans, contribution limits, and compliance requirements.
Tax Planning for Real Estate Investors: 2025–2026 Strategies
Navigate 2025–2026 tax changes as a real estate investor. 1031 exchanges, cost segregation, bonus depreciation phase-outs, and capital gains strategies.
From San Diego to Frisco: How Moving States Could Save You $130K+ a Year
High earners can save six figures by moving from CA to TX. See how no state income tax impacts your real take-home pay. Calculate your savings.
1031 Exchanges in 2026: How Real Estate Investors Defer $100K+
Real estate investors use 1031 exchanges to defer $100K+ in capital gains tax. With Congress debating changes in 2026, now is the time to understand how this strategy works.
The San Diego Surgeon's $60K Tax Problem (And the Strategy Most CPAs Never Run)
San Diego surgeons earning $500K+ could be overpaying $60K+ a year. Here's the year-round strategy most CPAs skip — and why California makes it worse.
The Entity Decision Costing Law Firm Owners $65,000 a Year (And the Retirement Move That Could Fix It)
Law firm partners earning $400K+ can save $95K+/year with the right entity structure and cash balance plan. Real numbers, real strategies.
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