Tax Guides

148 guides, built from the primary documents. Pick a topic to filter.

• All guides
• Trade contractors
• Job costing & pricing
• LLC & S-corp
• Self-employed & 1099
• Roth conversions
• Inherited IRAs
• Retirement
• IRS forms

• Trade contractorsJul 4, 202611 min

  When Should You Hire an Accountant or Bookkeeper — Not Just at Tax Time?

  For years the IRS has waived failure-to-file, failure-to-pay, and failure-to-deposit penalties for anyone with a clean three-year filing history — you just had to ask, and most people never did....

• Trade contractorsJul 4, 202610 min

  When Should You Consider an ESOP for Your Contracting Business? 2026 Exit Rules

  When should you consider an ESOP for your contracting business? You consider one when you run a profitable, stable company, you want to sell to your crew instead of an...

• Trade contractorsJul 4, 202611 min

  When Should You Become an S-Corp? The 2026 Income Trigger That Makes It Worth It

  The question every trade contractor eventually hits is when should you become an S-Corp trigger — the income level where the election becomes worth the added cost and paperwork. An...

• Trade contractorsJul 4, 202612 min

  What a W-2 Employee Really Costs in Taxes vs 1099 (2026)

  When you put someone on W-2, the wage on the offer letter is only the starting number. On top of it you owe 6.2% for Social Security (on wages up...

• Trade contractorsJul 4, 202617 min

  Transition From Handyman Work to a Licensed Contracting Business: 2026 Tax Guide

  If you're planning to transition from handyman work to a licensed contracting business, the tax and legal picture shifts the moment you cross the licensing line. The handyman exemption that...

• Trade contractorsJul 4, 20268 min

  SEP-IRA vs Solo 401(k) for Contractors: Which One Shelters More in 2026?

  Short answer: For 2026 both plans top out at $72,000, but they get there differently. A SEP-IRA can only reach that ceiling through the employer piece — up to 25%...

• Trade contractorsJul 4, 202613 min

  Should You Sell Your Contracting Business? What Makes It Worth Buying in 2026

  The question of whether you should sell your contracting business — and what makes it worth buying — comes down to one thing the buyer can verify: transferable cash flow....

• Trade contractorsJul 4, 202613 min

  Should You Bring Investors or Keep 100% Ownership of Your Contracting Business in 2026?

  If you're a trade contractor wondering whether you should bring investors or keep 100% ownership of your contracting business, the short answer is that outside equity is the most expensive...

• Trade contractorsJul 4, 202613 min

  Tax Write-Offs for Contractors: A 2026 Checklist for the Self-Employed Trade

  Here is the short version. If you are a self-employed trade contractor, almost every dollar you spend to do the work is deductible, and the code is more forgiving about...

• Trade contractorsJul 4, 202611 min

  Should You Hire Employees or Use 1099 Subcontractors in 2026?

  You've got a worker who keeps showing up — same crew, same jobs, week after week — and you've been paying them on a 1099. The business is growing, and...

• Trade contractorsJul 4, 202612 min

  Franchising a Home Service Business: Is It Worth It? 2026 Tax Guide

  If you're a trade contractor wondering whether franchising a home service business is worth it, the tax mechanics come down to three things: how the initial franchise fee is treated,...

• Trade contractorsJul 4, 202610 min

  Contractor Tax Audit Triggers: What Actually Flags Your Return in 2026

  Almost everything you've read about contractor tax audit triggers is aimed at the wrong thing. The IRS doesn't see your mileage log, your meal receipts, or whether you filed 1099s...