Flipping houses was big business during the housing boom. When the housing market took a turn for the worse, so did the finances of the flippers that had taken on a lot of risk. I’m a big fan of the buy and hold, quietly enjoying my passive rental income, but flipping houses appeals to a lot of people.
According to this article, the key to making money in flipping houses is threefold. The main thing to consider is the risk. This is main thing that devastated flippers after the housing crash. Other key points are to buy houses using CASH, move quickly, and buy homes that only need cosmetic fixing. Major structural repairs will almost never recover the costs when you sell and cause major delays in getting the house on the market (and remember one of the keys to success is to move FAST!).
My favorite couple in Portland has been successfully flipping houses through the good and the bad. The reason they are so successful is that they have a great eye for a diamond in the rough and are able to do almost all of the work themselves. What they lack in speed they make up for in man-power. If you are in the Portland area, I highly suggest you contact them (Tim and Jake) to ask them for advice.