Flip or not?

[John Warren]

Hello everyone!

My wife and I are trying to decide if we want to flip our first house later this summer. As back ground, we just closed on our first quad last month. This building will be cash flowing between $600-800 this month (now that the inspection stuff is fixed). I am also finishing up classes to become a real estate agent, and I should be licensed in a couple of weeks. By July we will have around $20,000 to work, not including our reserves. This should allow us to buy a house in this area of the Chicago suburbs that needs some work.

I am fairly handy, and I can install cabinets, countertops, toilets, replace windows and doors, etc. I am not a very good plumber, and I know it is not always optimal to do everything yourself, but I am on Summer vacation (school teacher) until August! I could definitely do some of the work and contract out anything that is above my pay grade.

I guess my question is what are some of the things we should be thinking about before we flip a house? Do we start looking for lenders who specialize in flipping? Do we need to start an S corp first? What am I overlooking?