I'm moving to Florida. I plan to buy a house that is 30k. Small bungelow. Just me, the wife, the dogs and a cat. At the same time I plan on buying a 55k fixer-upper.

The first I should be able to pay in cash. The second, won't get bought until my current home sells. However, that second house, once improved (by us: we do flooring, plumbing, painting and simple eletrical) should value at 160k.

Once we move to the fixed house, we'll rent the other for 500 a month. Should be doable since my wife is currently in FLA in a 300 sq/ft studio at 500 a month.

I purposely didn't want to go to the Bay for this reason. I avoid California at all cost for this reason. My long term plan is to startup a tech firm, hire college grads, train them and try to keep them with the company for 5+ years. Hard, but doable. The nice thing is they can get 45k a year, and get a pretty nice home/environment that would be hard to beat. So we'll see, but again the Bay really matters in the HN echo chamber.