#tax-planning
Tax Planning
Strategic tax planning to minimize liability and maximize savings
Roth Conversion Ladder: How FIRE Investors Tap Retirement Accounts Penalty-Free Before Age 59½
A Roth conversion ladder converts traditional IRA dollars to Roth in annual tranches, each unlocking penalty-free five tax years later — the core mechanism FIRE retirees use to tap pre-tax accounts before age 59½ while filling low tax brackets.
Rule 72(t) SEPP: How to Tap Your IRA Before 59½ Without the 10% Penalty
How Rule 72(t) Series of Substantially Equal Periodic Payments (SEPP) lets retirees tap an IRA or 401(k) before 59½ without the 10% early-withdrawal penalty — covering the three IRS calculation methods, the 5% interest-rate floor from Notice 2022-6, and the recapture-tax mistakes that bust early retirement plans.
Section 121 Home Sale Exclusion: How Homeowners Can Skip Up to $500,000 in Capital Gains Taxes
How Section 121 lets U.S. homeowners exclude up to $250,000 ($500,000 for joint filers) of capital gains on a primary home sale — covering the 24-month ownership and use tests, the two-year frequency rule, partial exclusions, depreciation recapture, and the nonqualified-use allocation.
Section 163(j) Business Interest Limitation: The 30% ATI Cap and OBBBA's EBITDA Restoration
OBBBA permanently restored the EBITDA-based ATI calculation for Section 163(j) starting in 2025, expanding deductible business interest for capital-intensive companies. A guide to the 30% cap, the ~$31M small business exemption, the 35% syndicate trap, EBIE allocations from partnerships, S-corp differences, and Form 8990 reporting.
Section 199A REIT Dividend Deduction: The 20% Tax Break Most REIT Investors Don't Fully Use
Section 199A lets investors deduct 20% of qualified REIT dividends from taxable income, dropping the top federal rate from 37% to about 29.6%. This guide covers Box 5 of Form 1099-DIV, the 45-day holding-period rule, Form 8995, and how OBBBA made the deduction permanent.
Section 25D Residential Clean Energy Credit: Final-Year Claim, Carryforward, and TPO Alternatives
Section 25D's 30% residential clean energy credit ends December 31, 2025 under the OBBBA. How to file the final-year claim on Form 5695, carry unused credit forward indefinitely, and use TPO leases or Section 48E to capture value in 2026.
Section 280E: How Cannabis Businesses Survive a 70% Effective Tax Rate
Section 280E bars cannabis businesses from deducting ordinary expenses, pushing federal effective tax rates past 70%. A walkthrough of the math, the COGS lever under Section 471, key Tax Court rulings (CHAMP, Olive, Harborside), and what 2026 rescheduling could change.
Section 280F Luxury Auto Depreciation Limits: The SUV Loophole and How to Maximize Your Business Vehicle Write-Off
Section 280F caps first-year depreciation on passenger autos at $20,300 in 2026, but SUVs and trucks rated above 6,000 lbs GVWR escape those limits and can combine a $32,000 Section 179 deduction with 100% bonus depreciation. A practical guide to the 2026 numbers, the heavy-vehicle and pickup carve-outs, the 50% business-use cliff, and the mileage-log standards an IRS auditor expects.
Section 831(b) Microcaptive Insurance: A Small Business Guide to Risk Management Without IRS Scrutiny
Section 831(b) microcaptive insurance lets small businesses retain underwriting profit on hard-to-insure risks, but the IRS's 2025 final regulations treat captives with loss ratios under 30% as listed transactions. Here is how to structure one that survives an audit.
The Short-Term Rental Tax Loophole: Offsetting W-2 Income Without Real Estate Professional Status
How short-term rentals sit outside the Section 469 passive loss rules, what the seven-day average and material participation tests actually require, and how a six-figure W-2 earner can use cost segregation and 100% bonus depreciation to legally offset wage income.
Spousal Lifetime Access Trust (SLAT) After OBBBA: Why the $15 Million Exemption Still Demands Action in 2026
After OBBBA set the federal estate, gift, and GST exemption at $15 million per person in 2026, SLATs still freeze growth out of the taxable estate at a 40 percent rate. Coverage of dual-SLAT reciprocal trust risk, asset selection, valuation discounts, and the audit records families need to keep.
Tax Loss Harvesting: The Year-Round Strategy That Can Save You Thousands in Capital Gains Taxes
Year-round tax loss harvesting can add 0.5%–1.5% in annual after-tax returns to a taxable portfolio. This guide explains the IRS netting order, the wash sale rule across taxable and IRA accounts, and a practical framework for harvesting short-term losses without losing the deduction.