Real Strategies, Not Internet Myths.
STR Loophole, REPS, S-Corps, Augusta, Solo 401(k)s—these are the real tools we use to help physicians, real estate investors, and business owners legally pay less over a lifetime, not just this April.
A guide by Taxstra Tax & Accounting — CPA-led tax strategy for business owners
Strategy Hubs
Three curated collections — start with the one that matches how you earn
You've probably heard bits and pieces: "buy an Airbnb," "start an S-Corp," "hire your kids," "do a 1031." The internet is full of tips, but almost none of them are integrated into your actual life. Real tax planning starts with your income mix, states, family, and time capacity — then layers in a handful of strategies that fit, documented so they survive contact with the IRS. Browse by hub below, jump to any strategy in the full library, or see how we implement all of this.
Real Estate
STR Loophole, REPS, Cost Segregation, 1031 Exchanges, and Bonus Depreciation.
For W-2 earners with rentals, full-time investors, and anyone buying or selling property.
View HubBusiness Growth
S-Corps, Hiring Kids, Augusta Rule, Accountable Plans, and Entity Structure.
For business owners, 1099 contractors, and anyone with self-employment income.
View HubWealth & Retirement
Solo 401(k), Cash Balance Plans, Backdoor Roth, and Tax-Loss Harvesting.
For high earners building tax-efficient wealth inside and outside retirement accounts.
View HubWhere to start
Most of your income on a W-2 and interested in property? Start in the Real Estate hub. Earning business or 1099 income? The Business hub covers entity structure first, deductions second. High income but thin deductions? The Wealth hub is about account structure, not spending. And if you'd rather skip the reading, the 30-minute call exists precisely to narrow this down to the two or three strategies worth your time.
Real Estate
Depreciation, passive-loss planning, and exit strategy for property owners
STR Loophole
How short-term rental owners can use losses against W-2 income without full real estate professional status — and the participation and documentation rules that make it work.
Real Estate Professional Status
The qualification tests for REPS, why returns claiming it get extra scrutiny, and how couples plan around one spouse qualifying.
Cost Segregation
How a cost segregation study front-loads depreciation deductions, when the study is worth the fee, and how it pairs with bonus depreciation.
Bonus Depreciation
What bonus depreciation covers, where the rules stand now, and how investors use it to create large first-year deductions.
Depreciation Recapture
The tax bill that surfaces when you sell a depreciated property — how it works and the planning moves that soften it.
De Minimis Safe Harbor
A simple election that lets you expense smaller purchases instead of depreciating them. What qualifies and how to claim it.
Business & Entity
Structure, compensation, deductions, and multi-state issues for owners and contractors
S-Corp Election
When an S-Corp election starts saving real money on self-employment tax — and how to run one cleanly once you elect.
Entity Structure
LLC, S-Corp, C-Corp, or partnership: matching your legal structure to your income, liability, and exit plans.
Entity Consolidation
When multiple entities help you and when they just multiply tax returns. How to simplify a tangled structure.
Accountable Plan
The IRS-recognized way to reimburse yourself for home office, phone, and mileage through your business.
Augusta Rule
Renting your home to your business for short stretches: how the rule works, who it fits, and the paperwork that matters.
Hiring Kids
Paying your children for real work in the business — what counts as legitimate, and how to document it.
Home Office Rules
The simplified and actual-expense methods, who qualifies, and how to claim a home office cleanly.
QBI §199A
How the qualified business income deduction works, where the phase-outs bite, and the planning levers for high earners.
Solo 401(k)
The retirement plan built for owner-only businesses: contribution mechanics, Roth options, and setup timing.
Late S-Corp Election
Missed the election deadline? The relief procedures that may let you elect S-Corp status retroactively.
Locums S-Corp
Whether an S-Corp makes sense for locum tenens physicians, and how to structure 1099 contract income.
Moonlighting Structure
How physicians with side 1099 income should structure, deduct, and pay estimates on moonlighting earnings.
Reasonable Compensation
How to set an S-Corp salary that satisfies the IRS without giving back the tax savings.
Fringe Benefits (S-Corp)
Which benefits stay tax-advantaged for S-Corp owners, which don't, and how health insurance runs through payroll.
Fringe Benefits (C-Corp)
The wider menu of benefits available to C-Corp owner-employees — and when it justifies the structure.
Owner Basis Management
Tracking stock and debt basis so distributions and loss deductions don't trigger surprise taxes.
R&D Tax Credit
Who actually qualifies for the research credit (it's not just tech), and the documentation a claim needs.
PTET Workaround
How pass-through entity tax elections work around the SALT deduction cap, state by state.
Sales Tax Nexus
When selling across state lines creates sales tax obligations — and how to get compliant before it snowballs.
Multi-State Nexus
How working or earning in multiple states creates filing obligations, and how to avoid paying tax twice.
Partner Buy-In / Buy-Out
The tax mechanics of buying into or out of a partnership — structure the deal before you sign it.
1099 / Side Gig Optimization
Deductions, quarterly estimates, and entity choices for contractors who want to keep more of their 1099 income.
Wealth & Retirement
Account design, Roth strategy, and equity compensation for high earners
Tax-Loss Harvesting
Turning portfolio losses into tax assets without tripping the wash sale rule.
Roth Conversions
When converting pre-tax dollars to Roth makes sense — and how the backdoor Roth works for high earners.
Mega Backdoor Roth
Using after-tax 401(k) contributions and in-plan Roth conversions to route an extra $30K–$40K into Roth each year.
529 Superfunding
Front-loading multiple years of education savings into a 529 at once, using the gift-tax rules built for it.
AMT Planning
Who still gets caught by the alternative minimum tax — especially with incentive stock options — and how to plan around it.
Asset Location
Placing the right assets in the right account types to reduce the annual tax drag on your portfolio.
Bunching Deductions
Timing charitable gifts and other itemized deductions into alternating years so they actually count.
HSA Strategy
Using a health savings account as a long-term, tax-advantaged investment vehicle — not just a medical checking account.
NUA Strategy
Net unrealized appreciation: a special treatment for employer stock inside a 401(k) — when it applies and how to evaluate it.
Equity Compensation
RSUs, ISOs, and ESPPs: how each is taxed and the timing decisions that prevent expensive surprises.
DB vs DC Plans
Defined benefit vs defined contribution plans — and how cash balance plans let established owners shelter far more.
QSBS §1202
The qualified small business stock exclusion: who qualifies, and what founders should confirm before selling.
PSLF Filing Status
How filing-status decisions interact with income-driven repayment and Public Service Loan Forgiveness.
Charitable & Estate
Giving and wealth-transfer structures that do double duty on taxes
Charitable Remainder Trust
Converting appreciated assets into an income stream, a deduction, and a future charitable gift.
Charitable Lead Trust
Front-loading charitable impact while moving assets to heirs tax-efficiently.
Qualified Charitable Distribution
Giving to charity directly from your IRA — who's eligible and how it interacts with required distributions.
Family Limited Partnership
Transferring wealth across generations through a family partnership — and the guardrails that keep it defensible.
Tax Strategy FAQ
The questions people ask before committing to a strategy engagement
Ready To Turn Strategy Into Action?
You don't need every trick in the code. You need a specific set of moves that match your life, executed cleanly and repeated year after year. If we don't see meaningful, defensible savings in your situation, we'll tell you that directly.
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