Tax Strategy Blog
Actionable strategies for real estate investors, business owners, and high earners — written by the Roadmap Tax team.
How to Diversify RSUs Without a Tax Catastrophe
Learn how to diversify RSUs without a tax hit. This guide covers multi-year sell-down plans and donor-advised funds to minimize capital gains for tech execs.
Should Your Medical Practice Own the Building? Entity Planning for San Diego Physicians
Should your medical practice own the building or hold it separately? A San Diego tax strategist walks through the entity math for physicians earning $400K+.
Can You DIY a Cost Segregation Study? The Real Answer for Property Owners
Learn why a DIY cost segregation study risks IRS audit and how professional engineering standards protect your accelerated depreciation deductions.
Tax Planning Services: What a Tax Strategist Does Month by Month
What tax planning services provide for high earners and business owners: entity structure, retirement, cost segregation, and equity comp explained.
Roth IRA Conversions for High Earners in 2026: When They Make Sense and When They Don't
A practical framework for high earners deciding whether to convert an IRA to a Roth. When it works, when it doesn't, and how California tax affects the math.
The 60% Trap: Why Your 401(k) Alone Can't Protect Your Retirement Income
Most high earners max their 401(k) and assume they are set. The 60% trap means retirement income gets taxed at 40-60%. How to plan around it.
How Much to Pay Kids Tax-Free From Your Business in 2026
If you run a profitable business, hiring your child can shift income tax-free up to the standard deduction. How the 2026 rules work for business owners.
When You Sell a San Diego Rental Property, a 1031 Exchange Defers the Capital Gains Tax
A 1031 exchange defers the capital gains tax when San Diego investors sell rental or commercial property. How it works and what 2026 changes could mean.
What a Customized Tax Strategy Covers That Your Preparer Doesn't
A tax preparer files your return. A tax strategist designs your outcome before the year closes. Here's what a customized tax strategy includes for high earners.
Ready to build your tax strategy?
Reading is a start. A call with the Roadmap Tax team turns these strategies into a plan built around your entities, income, and goals.
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