DEAR BRIAN: I love real estate. I've flipped a few houses in my day, too. But the particulars of the deal make me a little nervous.
In a situation like this you need to do a basic business analysis. You've got to have a plan and figure out the worst case scenario. Part of this is determining whether or not you can survive if things fall apart. In this case, the worst case is that you can't get a renter and the house doesn't sell. It puts your family in jeopardy if this happens, so to me it's not an option.
Lots of people have had the same idea, with the best of intentions, and still end up in a big mess. But if you and your wife are willing to accept the possibility of things not working out like you planned — and the fact that you might have to take additional jobs for an unknown period of time just to make ends meet — then it might be a play. I don't like putting myself into skin-of-my-teeth positions intentionally. Any deal that runs the risk of leaving you bankrupt, or the victim of a foreclosure, just isn't worth it.
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