I guess there are trade offs though because naturally banks would be a bit more resistant to lend to a LLC unless it had a whole lot of money in the bank.

But see, that is my point, these are just details, yes there bewildering nature may look a lot like concern but there is no concern, query yes, uncertainty a plenty for sure, but concern not so much. 

We should have been able to recognize earlier on that the work being performed was not adequate. 

Would the natural progression still be a mailers and skip trace route?

Be sure to have a solid tax advisor and understand the calculations and systems in each region you’re interested in.Also, the natural disaster risk you mentioned is very real.

You might find a deal where you’d end up with adequate reserves with a favorable loan you weren’t previously aware of.

Most self-directed IRA firms are administrative in nature and hold required licensing that is more banking related in nature. 

@Michael PempinI don't know even the general nature of your transaction so I can't comment anymore on your estimates.As for your question about why leverage on when your property may go down and why buy more now...

@Richard Damian Awesome and what type of homes are you looking for, two bed rooms three bedrooms things of that nature.

In Chicago it is illegal to deny a sublet, so as long as you find an adequate replacement tenant you can move out anytime during your lease, offering flexibility with your purchase timeline