I have “flipped” properties successfully (never homes though, always land or commercial pieces that were obviously undervalued due to economic mismanagement) but was always prepared to hold the property and operate it profitably if I couldn’t realize my intended profit.
I would never take on a deal entertaining the notion that I might lose money with it, by either selling at a loss or operating it with negative cash flow. The “flip mentality” that surfaced in this last run-up of residential real estate values was very dangerous to the novice real estate “investor” (almost everyone in the market recently), if you can even use that word with a house flipper.
I am simply amazed at how cavalier some people are thinking they can get rich quick, especially in a market that is obviously topping or at best slowing considerably. I guess it’s the greater fool theory gone awry.
Loss is always a consequence of greed. And in real estate, as with any investment, good planning (always with a fall back position) along with precise timing is everything.