My long term goal is positive cash flow as I intend to own the home for 30+ years and appreciation discounted over that period of time makes very little difference to the return I make; it's more about the rental income compared to the total cost of the house for me.  

Getting it rezoned is really the only way to go and that's not guaranteed.

In most cases, they just don't trust the investor.What are investors trying to accomplish with "buy like rent, lease option, option", In most cases it is to BUY TIME to find an assignee or to flip the property.Here are some ideas you may want to try on for size:Write a contract of sale (I use a skinny contract, one that anyone can read and understand in a few minutes) with a delayed settlement (for as long as you can negotiate), with right of possession or if occupied right of entry), and "subject to the existing mortgage"Skinny contract of sale with a Study Period, with right of possession or if occupied right of entry.Make full disclosures 1.

I have a pretty short inspection period and it is a holiday week, so hopefully either Marc or Kibbe will be available early this week.  

For the sake of discussion, let's say that your future investor would pay $250k in today's dollars because he knows it will be nearly worthless by the time he comes to sell.Now you have to figure out how much money you have to make over your ownership period for the investment to be worthwhile.

You're entitled to the full UPB plus advances plus costs, so in that example if the house is worth 200k+ and your UPB is 100k then you're pretty much guaranteed to recoup the full amount.

Usually over a 10 year period I see a top and the bottom when most areas fell in 2007.

What threatens Chicago is the city's debt burden.W/ all of that said,  I've never been a big believer in trying to predict/time the market because I'm guaranteed to be wrong.  

If you sign a contract that you do not fulfill you are subject to claims against you......period!

Those paying 6 caps probably expect an extended period of low rates, and want the added benefit of some inflation protection (rents tend to rise with inflation).