Tax Planning

You Built the Asset. Now the IRS May Tax the Sale as Ordinary Income

If you personally created certain IP, the gain on sale can be ordinary income, not capital gain. The fix is not “hope.” The fix is planning, structure, and allocation.

Portability Is Not Automatic, And One Mistake Can Zero It Out

Portability can be the simplest way to preserve a married couple’s combined exclusion, but one Form 706 mistake can erase the DSUE amount. The most common failure is using simplified reporting when the estate plan requires real asset values.

Section 179 vs Bonus Depreciation After OBBBA: What Actually Matters

100 percent bonus depreciation is back and Section 179 limits are larger, but Section 179 has income limits and carryover mechanics. Here is the decision screen.

HSAs After Death: The Tax Trap Most Families Miss

If your HSA beneficiary is not your spouse, the account can become taxable income in the year of death. This briefing explains the rules and the documentation driven mitigation options.

A Little Known Way to Pay Family Without Payroll Taxes

Most “hire your child” strategies rely on payroll. A cleaner alternative can be a one time project payment that shifts income to a lower bracket without payroll taxes, if structured and documented correctly.

Spouse Employee 105 HRA: Do You Need a W-2, or Can the Reimbursements Stand Alone?

A spouse employee 105 HRA can be supportable without W-2 wages in some cases, but zero wages plus large benefits can look unusual. Adding wages improves optics but triggers payroll compliance and penalty exposure.

Brutal IRS Trap: The Receipt Mistake That Wipes Out Goodwill Clothing Deductions

You can donate real value and still lose the entire deduction. The trap is not the charity. It is the paperwork: generic receipts and an incomplete Form 8283 can zero out the write off.

Tax Preparer Fraud Can Keep the IRS Audit Door Open Indefinitely

The three-year audit clock is not always a clock. In certain fraud situations, the IRS can argue the year stays open indefinitely, even if the taxpayer relied on a preparer.

The Employer Childcare Credit Just Became a Strategic Planning Tool (2026 Update)

Beginning in 2026, the employer provided childcare credit expands significantly. For closely held businesses, this may shift childcare from a benefit to a strategic tax planning opportunity.

2025 Crypto Tax Reporting Is Changing: What Form 1099-DA Means for Investors

Crypto tax reporting is entering a new phase. Starting with the 2025 tax year, custodial platforms will report digital asset transactions to the IRS on new Form 1099-DA. Here’s what investors need to understand now to avoid surprises and stay compliant.

2025 Year-End Crypto Tax Strategies: Smart Moves Before December 31

Crypto gains can create unexpected tax bills, especially in profitable years. Before December 31, several planning opportunities can help reduce your 2025 taxable income, strengthen your long-term position, and keep more of your returns working for you.

2025 Year-End Tax Strategies for Investors: Smarter Moves for Your Stock Portfolio

The final weeks of the year offer a valuable chance to lower taxes on your investment gains. By adjusting how you recognize gains and losses, using charitable giving strategically, and understanding the rules that apply to stock sales, you can reduce your 2025 tax bill without changing your overall investment goals.