Tax Strategy Blog
Actionable strategies for real estate investors, business owners, and high earners — written by the Roadmap Tax team.
Your Short-Term Rental Is Depreciating Over 39 Years. It Doesn't Have To.
Most short-term rental owners depreciate their property over 39 years. A cost segregation study can accelerate that timeline dramatically in 2026.
San Diego Tax Guide 2026: What High Earners Need to Know
How living in San Diego affects your tax bill in 2026 — from CA's 13.3% top rate to SALT limits, Prop 13, and whether moving to Texas really saves money.
Your RSUs Vested in June. Your Preparer Won't Call Until March.
RSUs vested in June but your tax preparer won't call until March — that 9-month gap leaves tech executives reacting to outcomes they could have designed. A scenario walkthrough.
7 Tax Strategies for San Diego High Earners & Business Owners in 2026
California taxes hit hard. Here are 7 tax strategies for San Diego high earners and business owners to cut their 2026 tax bill — legally and locally.
You Can't Change the 22% RSU Withholding. Here's What You Can Do Instead.
Your company withholds 22% on RSUs. If you're in the 35% bracket, that leaves a gap of nearly $78K a year. Here are two ways to close it before April.
The 3.8% Tax Nobody Mentions When You Sell RSUs to Diversify
RSU diversification sales trigger the 3.8% Net Investment Income Tax. Here is how it works, what it costs, and three strategies to plan around it before April.
The 22% RSU Withholding Worked Before 2026. Here's Why It Doesn't Anymore.
The TCJA rates expired. Your 22% RSU withholding now leaves a wider gap than before. Adjust Q3 estimated tax before the September 15 deadline.
Your Q3 RSUs Vested. Fix Your Estimated Tax Before September 15.
Your RSUs vested in Q3 and 22% withholding won't cover the real tax. Here's how to adjust your September 15 estimated payment and avoid an April surprise.
Why Holding RSUs After They Vest Creates a Second Tax Bill (and What to Do About It)
Your RSUs vested and you held. Now there's a capital gains tax waiting when you sell. Here's how the mechanics work and how to plan ahead.
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