Hiring your child can create more than a business deduction. Entity structure, payroll taxes, documentation, Section 199A, and the child's earned income can materially change the result.
Multiple businesses can create a Section 199A problem that is easy to miss. When income, wages, property, and losses sit in different entities, calculating each business separately can produce a very different result from a permitted aggregation.
Selling a property at a loss tells you the economic result. It does not necessarily tell you the tax result. How the property was acquired, improved, marketed, and held can materially change the treatment.
Receiving a long-awaited Employee Retention Credit refund may not close the file. If the related wage deduction was never adjusted, current IRS guidance may create an income-tax consequence in the year the refund arrives.
A major sale can create one of the largest tax events of an owner's financial life. The critical planning question often isn't what to do after closing - it's what needs to be evaluated before the deal becomes binding.
One of the most common reasons business owners never claim the home office deduction is surprisingly simple; they assume their home isn't large enough. That assumption may be costing them more than they realize.
Some tax strategies gain popularity because they sound logical. But when the numbers are analyzed, the expected tax savings often disappear. Here's why buying assets personally and renting them to your corporation may not deliver the benefit many business owners expect.
Health insurance is one of the largest deductions available to many S corporation owners. But the deduction depends on more than paying the premium. Reporting, payroll, and eligibility all matter.
Inventory can quietly delay tax deductions. Some qualifying small businesses may have options to deduct inventory-related costs sooner, but the accounting method and records must support the position.
Many real estate investors assume unused rental losses disappear forever. They usually do not. The real planning question is not whether the deduction exists. It is whether your future decisions allow you to use it.
Two partners can pay the same business expense and receive different tax treatment. The difference is often not the expense itself. It is whether the partnership agreement allows reimbursement or requires the partner to bear the cost personally.
Many business owners spend money before a business opens and assume the deduction follows. The IRS often applies different rules. Timing, classification, and entity structure can determine whether a deduction is available now, later, or not at all.
Many business owners spend years minimizing annual taxes through an S corporation. Few stop to ask whether that same structure could affect the tax consequences of a future business sale.
A charitable donation can be completely legitimate and still produce a zero deduction. For non-cash charitable donations exceeding $5,000, one missing appraisal or documentation error can erase the entire write-off.
A one-time payment to a child or family member can create valuable tax benefits. The bigger risk is incorrect reporting, which can trigger kiddie tax issues, 1099 mistakes, and lost IRA opportunities.
A quiet 2026 tax change eliminates the deduction for common workplace perks. Many employers haven’t adjusted. Here’s what’s now fully nondeductible; and what you can still structure correctly.
Most business owners deduct church and charity gifts the wrong way. In 2026, proper structuring may convert certain payments into fully deductible business expenses.
Rent your home to your S corporation for 14 days or less and the rental income may be tax free. Here is how the rule works, where it fails, and how to document it properly.
If you pay $500 at a school auction for something worth $200, only $300 may be deductible. Here is how the rule works, who sets fair market value, and how to avoid losing the deduction.
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.
