I've had an online resale business since 2004. I file schedule C on all items I buy with the intent of reselling for a profit. I've paid hundreds of thousands of self employment income taxes. I also have a separate selling account I use for the odd personal item I'm selling off that I no longer want. Most of those are sold at a loss. A few at a profit. Those sales are the ones that are now going to cause me a headache. Some are $5-10 items like used books, but others can be $500+. A couple weeks ago I sold the tumbler I used when restoring my TAF. Paid $340 for it. Cleared about the same after fees and shipping. That's the type of sale I don't want to report.