I tend to oversimplify taxes and overcomplicate everything else. If you buy an asset thinking you'll sell it when it appreciates without you working on it, you're an investor (Sch D). If you buy a house to fix up and you think your work (including the work you do to hire the other people who work) will lead to income, you're a dealer (Sch C). Yeah, I lose a few clients being like this, too. Not many, but I'm fine with it. The last one qualified for EITC whether I used Sch C or Sch D, but I hope she had an investment gain that knocked her right out of it the next time she fixed up a house, and the guy who amended my return lost sleep over it. What to do, what to do... Yeah, I know, he didn't, but still...