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.  

I am broke, a full-time college student, part-time worker, and up to my neck in debt.

On the other side, there is enough concern about rates going up that there aren't people willing to lend into this space at less than 5% on long term money, especially since debt gets deflated with inflation.

However, my lawyer pointed out the lender does not allow the transfer to the third party/LLC and transfer could cause an acceleration of the debt (requiring me to pay the entire debt on demand).

The debtor's bankruptcy attorney will counsel them on what they can and cannot enter into, a lease would be something to have approved as it is an ongoing debt obligation and the Trustee will need that to determine what amounts are available for creditors.There is no sneaky way of taking any significant amount of money from a debtor during this period as they are under an audit of their assets and liabilities.

Debt structure has loosened up some on commercial but not to the extent before the last downturn.

We have not talked numbers or financing yet but he said I can bring in an inspector to take a look around.The last piece is that I'm self employed, earning around $30k a year, no debt, around $35k in cash I'm willing to invest, though I would prefer not to spend it all on one property.  

@Tim G.How good would your credit need to be to get those loans and what debt to income ratio need to be for you to get approved ?

Just like humans, some properties are a lot more low-maintenance than others.Your entire mortgage payment does hit cash flow, but technically the principal repayment portion is not an expense (it is repayment of debt).  

However it was easy for us cuz we had NO personal debt.