Are You a Real Estate Dealer or Investor? Why It Matters More Than You Think

Episode Description: In this episode of How to Lower Your Tax Bill, Terrence Hutchins explores a key distinction that could dramatically affect how much tax you owe on your real estate income: are you a dealer or an investor? If you’re flipping houses or building a rental portfolio—or doing both—how the IRS classifies your activity can mean the difference between capital gains taxes or ordinary income plus self-employment tax.

Terrence walks through how the IRS makes this classification, what the tax consequences are, and what you can do to protect your profits. He also shares a powerful seven-point filter for analyzing real estate investments and wraps up with a fascinating tax court case that could help you if the IRS challenges your classification.

Key Topics Covered:

• The seven-part filter to assess real estate deals: risk, upside, tax treatment, control, effort, time, and fees
• Dealer vs. investor classification and how the IRS determines your status
• Why your intent and documentation matter more than your titles
• The tax impact:
  • Dealers pay ordinary income tax and self-employment tax
  • Investors pay long-term capital gains tax (if held more than a year)
  • Dealers can’t use depreciation or 1031 exchanges—but investors can
• How to avoid accidentally being classified as a dealer
• Tips for structuring your real estate activity: use of LLCs, separate accounts, tracking time, and keeping records
• When using an S corporation might help flippers reduce self-employment tax

Featured Tax Case: In Byron v. Commissioner, John Byron sold 22 real estate properties over three years, netting $3.4 million. The IRS classified him as a dealer—but the court disagreed, citing his lack of active marketing, minimal involvement, and intent to hold for investment. The result? Byron paid capital gains tax instead of a much higher ordinary income tax rate.

This case highlights why documentation and strategy can make or break your tax outcome.

For more real estate tax tips, subscribe to How to Lower Your Tax Bill on Spotify or Apple Podcasts. And as always: Keep More of What You Earn.

#KeepMoreOfWhatYouEarn