Insights on tax, equity, and building wealth
Guides and analysis from the Harness team and the advisors on the platform.
Year-End S-Corp Review: Still Right for 2027?
Run the S-corp numbers now, before the March 15, 2027 deadline. Learn when election status stops paying off and how to revoke it (IRC 1362(d)).
Restricted Stock and 83(b): What Happens If You Miss the 30-Day Window
The 83(b) election deadline is 30 calendar days with no extensions. Here’s what happens if you miss it, and how the new e-filing option (Form 15620) works.
Short-Term Rental Owners: Year-End Documentation for Material Participation
Relying on the STR loophole this year? Here’s the material participation documentation to finalize before December 31 — hours, logs, and vendor tracking.
Open Enrollment 2027: Choosing Between an HSA and FSA
HSA or FSA for 2027? Compare contribution limits, HDHP thresholds, and use-it-or-lose-it rules before you lock in your open enrollment choice.
Extended Deadline Day: What Crypto Investors on Extension Still Need to Report
Filed a tax extension? October 15, 2026 is here. Here’s exactly how crypto sales, staking, and airdrops need to be reported before you file
Filed for an Extension? Your October 15 Deadline Checklist
October 15 is your final filing deadline if you extended. Here’s what’s still due, what penalties may already be accruing, and what to do now.
AI for the Practicing CPA
In case you missed Bhanush Arora’s NYCPA session, here are the slides from “AI for the Practicing CPA.” It’s a practical look at where AI helps a tax practice, where it creates risk, and how to start with a 90-day adoption plan.
ISO Exercise and AMT: Year-End Planning for Stock Option Holders
ISO exercises can trigger a hidden AMT bill under IRC 56(b)(3). Learn the 2026 AMT exemption amounts and the year-end ‘crossover’ fix if your stock has dropped.
1031 Exchange Timelines: Why Q4 Is the Riskiest Time to Start
A 1031 exchange started in Q4 can lose weeks of its 180-day window to your tax filing deadline. Here’s the rule, the math, and the fix.
Fourth-Quarter Tax Review: Close Your Books, Skip Surprises
Q4 is the last window to catch tax problems before December 31. Use this checklist to review income, estimates, and bookkeeping now.
How Much to Contribute to Your 401(k) Before Year-End to Hit the 2026
The 2026 401(k) limit is $24,500 ($32,500 at 50+, $35,750 at 60-63). Here’s the paycheck math to hit it before December 31.
Reconciling Crypto Cost Basis Before New 1099-DA Rules
Form 1099-DA cost basis reporting starts in 2026. Here’s why your broker’s numbers may not match your records — and how to fix it before you file.
Planning Q4 RSU Vesting and Stock Sales Before Year-End
Q4 RSU vests are taxed at a flat 22%/37% rate that often under-withholds high earners. Here’s how to true up before the Jan 15 deadline.
Bought Rental Property This Year? Your Q4 Cost Seg Timeline
Bought a rental property in 2026? Here’s the realistic Q4 timeline for a cost segregation study, how 100% bonus depreciation factors in, and what it costs.
Q3 Estimated Taxes Are Due September 15: A Last-Minute Checklist
Q3 2026 estimated taxes are due September 15. See how much to pay, how the Form 2210 penalty works, and what to do if you’re already late.
S-Corp Election Timing: When It Helps — and When It’s Just Extra Complexity
S-Corp election can cut self-employment tax, but payroll costs and IRS scrutiny add up. See the math, the Form 2553 deadline, and when it pays off.
Planning Alert: What Business Owners Should Do Now, Before the Fall Tax Deadline
Fall is the real deadline for year-end tax planning. See what to lock in now on entities, retirement plans, equipment, and estimates before Dec. 31.
HSAs as a Stealth Retirement Account: The Triple Tax Advantage Explained
An HSA offers a tax break no retirement account matches — deductible in, tax-free growth, tax-free out. Here’s the 2026 limits and the retirement play.
Trump Accounts Explained: The New Tax-Advantaged Savings Vehicle Launching in 2026
Trump Accounts let families save up to $5,000/year per child, tax-deferred. Here’s the $1,000 seed deposit, employer rules, and deadlines for 2026.
Mega Backdoor Roth in 2026: Who Should Still Use It After OBBBA
The mega backdoor Roth still works in 2026 — up to $47,500 in after-tax 401(k) space. Here’s who qualifies, what OBBBA changed, and the catch.
Real Estate Professional Status: Qualifying Rules and Common Mistakes
The two-part 750-hour test for real estate professional status under IRC 469(c)(7), material participation rules, and the documentation failures that sink audits.
1031 Exchanges vs. Delaware Statutory Trusts: Which Deferral Strategy Fits Your Portfolio
Compare direct 1031 exchanges and DST replacement properties — deadlines, control, minimums, and liquidity — before your next real estate sale.
Cost Segregation Studies: Accelerating Depreciation on Investment Property
How a cost segregation study reclassifies building components for faster depreciation, works with 100% bonus depreciation, and what recapture means at sale.
Crypto Tax-Loss Harvesting in 2026: Does the Wash Sale Rule Still Not Apply?
Crypto still isn’t subject to the wash sale rule in 2026 — here’s how the loophole works, why it’s survived multiple repeal attempts, and how long it might last.
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