Brian Caldwell
Enrolled Agent (EA), Former Senior Tax Preparer at H&R Block
Brian Caldwell is an Enrolled Agent authorized to represent taxpayers before the IRS. He has prepared over 5,000 individual and small business tax returns across every major filing platform. Brian tests tax software the way real filers use it — with W-2s, 1099s, Schedule C income, and itemized deductions — to evaluate accuracy, audit risk, and whether the "free" tier is actually free.
Articles by Brian Caldwell
Vehicle Tax Deductions: Mileage vs Actual Expenses
The standard mileage rate for 2026 is 67 cents per mile. Actual expenses include gas, insurance, repairs, and depreciation. Learn when each method saves more and how to switch between them.
Estimated Tax Payments: How to Calculate and Pay
Self-employed workers and those with significant non-wage income must make quarterly estimated tax payments. Learn how to calculate your payments, due dates, and how to avoid penalties.
Dividend Taxes: Qualified vs Ordinary Dividends
Qualified dividends are taxed at capital gains rates while ordinary dividends are taxed as regular income. The holding period determines which rate applies to your dividend income.
State Tax Reciprocity Agreements Explained
If you live in one state and work in another, reciprocity agreements may save you from filing two state returns. See which states have agreements and how to claim exemption.
IRS Penalties: Late Filing, Late Payment, Accuracy
The IRS imposes separate penalties for late filing, late payment, and accuracy issues. Failure-to-file penalties are 10 times steeper than failure-to-pay. Learn the rates and how to avoid them.
Currently Not Collectible Status: IRS Hardship
If you truly cannot afford to pay, the IRS may place your account in Currently Not Collectible status. Collections stop temporarily while the statute of limitations continues to run.
How Filing Status Affects Your Tax Rate
Your filing status determines your tax brackets, standard deduction, and eligibility for credits. Choosing the wrong status can cost thousands. Understand all five options.
How to Respond to an IRS Audit Notice
Receiving an audit notice is stressful but manageable. Learn the types of audits, what documentation to gather, your rights during the process, and when to hire professional representation.
Property Tax Appeals: How to Lower Your Bill
Property taxes are based on assessed value, which can be wrong. Learn how to file a property tax appeal, gather comparable sales data, and negotiate a lower assessment with your county.
States With No Income Tax: Pros and Cons
Nine states charge no income tax, but many make up for it with higher property and sales taxes. Compare the total tax burden before relocating to a so-called tax-free state.
City and Local Income Taxes You Might Be Missing
Some cities and counties levy their own income taxes on top of state and federal. New York City, Philadelphia, and others add 1-4% to your tax bill. Learn where local taxes apply.
Education Tax Benefits: 529 Plans Explained
529 college savings plans offer tax-free growth and withdrawals for education expenses. Some states also give a deduction on contributions. Here is how they work.