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Eighteen years is a long time, but not in respect to 9/11 as that day remembered by Americans seems like recent memory. As a former NYC firefighter my memory is reinforced everyday. Seeing the children of friends lost that day, now grown up, hearing the hoarseness in the voices of friends who now have permanent respiratory illnesses, and talking to those who are continuing rounds of chemo therapy and radiation, 9/11 is present in daily lives of so many firefighters and police officers. Remembering the days after 9/11 there was a shower of kindness from around the world. Firehouses were decorated with flowers, messages, and photos. People brought food with tears in their eyes, and hugs were all around us, there were a lot of hugs. Firefighters let it be known to the wives and children of those lost that they now have many surrogate fathers in the firehouse who will always be there for them. This continues to this day as we've watched the children grow up, go to college, and get married. We're still there for them. Please keep all those lost and their families in your prayers, they still need it more than ever. Never Forget, Bill

Thanks, Bill... for who you are. Praying always.

We will keep you, those lost, those not, and those still struggling, in our prayers, Bill. Thanks so much for all that you and they did. And we won't forget...

Bill said it....Thanks Bill.

Also helped by *amazing* tech support that gets you the answer to any question you have, fast.

I think all the guys' answers above (maybe yes, maybe no) are right on the mark. There's no bright line and mostly it's a matter of luck whether IRS reels him in (chances are good you'll be okay with a "D" nowadays). It's better to let the client decide (unless you can't count the houses on one hand) and get them to sign off on it. One thing I'm pretty sure of -- after you advise SE would be due, the majority will maintain those flips were incidental and no business was involved.

This topic usually ends with someone being 100% sure everyone else is wrong.

There is no guide to determine investor, or dealer. It is all based on facts and circumstances, intent and a pattern of behaviour. It seems to me that flipping 3 houses in two years would classify him as a dealer. This might help. https://rsmus.com/what-we-do/services/tax/the-dilemma-of-dealer-or-investor-classification-for-real-estate.html