Brian Caldwell
Editor-in-Chief
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(12)
Best Tax Software for Self-Employed 2026: TurboTax, H&R Block, and FreeTaxUSA Compared
You filed your first 1099 last year and the deductions you missed cost you real money. The right tax software for self-employed filers in 2026 ranges from $0 (FreeTaxUSA) to $129+ (TurboTax). Here is the honest ranking.
Best Tax Software for 1099 Contractors and Gig Workers 2026: Honest Picks
You drove Uber, freelanced, or contracted last year and your tax situation got messy. The right software for 1099 and gig workers in 2026 spans $0 to $129 — but the price is not the same as quality. Here is the honest ranking.
Business Meal Deductions: What Is Allowed in 2026
Child Tax Credit 2026: Eligibility and How to Maximize It
TurboTax vs H&R Block vs FreeTaxUSA 2026 Comparison
Freelancer Tax Deductions: The Complete List for 2026
Earned Income Tax Credit Eligibility: Complete Guide 2026
Estimated Tax Payments: Who Owes and When to Pay
Every Landlord's Tax Deduction Guide Review: Essential for Rental Owners
Stephen Fishman's 750-page landlord reference covers Schedule E, depreciation, repairs-vs-improvements, passive-loss limits, and 1031 exchanges with worked examples.
Sooez 13-Pocket Accordion File Organizer Review: Letter-Size Full Archive Option
Unlike small receipt folders, Sooez's letter-size 13-pocket expands to hold full 8.5×11 documents — the right tool for storing a year of returns, W-2s, and bills.
LLC & S-Corp Mastery Guide 6-in-1 Review: Breadth Over Depth
Hiyasat's 6-in-1 bundle covers entity choice, formation, tax strategy, and growth in one package — useful for year-one entrepreneurs, less deep than dedicated Nolo titles.
H&R Block Deluxe + State 2025 Review: The TurboTax Alternative That Costs Less
H&R Block's Deluxe tier covers the same deduction and investment scenarios as TurboTax Premier at meaningfully lower pricing, with strong audit support and five free federal e-files.