Usually living in it for a few years may be enough for it to cash flow positive when you move out.  

I'm looking to finance the project long term in a way that is helps me create positive cashflow.

i wouldn't tell you where you should move since i don't know you.also, a lender would be in the best position to advise whether you qualify for a specific loan. 

Perhaps it has something to do with the statistical average where in Australia, if you are borrowing 75% on property in the cities or suburbs, it is almost impossible to get positive cash flow ANYWHERE, whereas BP subscribers are aware that in MANY parts of the USA, the opposite is true.

I didn't follow the impacts on the housing market though.Great website. 

He's on facebook and has a website for contact info.

Your cash flow is positive on paper, but how will that look in reality?

I plan on getting a property every year until I retire if I can find a good deal that cash flows positively.

Given that I'm not positioned to buy just yet, and simply running the numbers, is there a rule of thumb for estimating insurance costs that would make sense in Cook County?

I'm currently building out my foundation (website, SOP's, etc).