It's no more speculation to assume my numbers than the numbers that you are hoping for to remain the same.I know my planned returns, you are hoping yours don't change because you don't have the rent growth or appreciation to to cover the inflation and capex expenses over the long term. 

Be prepared to bring buyer down to a local mortgage bank and open a savings account for building a verifiable down payment.5.

How dumb do you have to to be not to understand that?

@Bara NwokomaWith the property address you can go to the Tax Assessor's site and verify the current state of the taxes, because I'm having a hard time believing they haven't been auctioned before now.Also, have you checked DCAD or TAD to verify the person you're speaking with is actually the property owner?  

Without doing a credit/background check You have no way to verify past rental history or credit.

SewerCapEx reserve - which you will definitely need in a building that old in Chicago.Due diligence - you need to verify everything - rent rolls, leases, utility bills, property tax bills, recent CapEx, etc.  

How do you structure a cosigner/guarantor for a tenant (recently graduated student) that has zero credit history, but who has excellent verifiable income.

It just goes to show you that your never too old to learn new or better ways to to do things.

Seller owes $60K of back taxes (has not paid taxes for the past 6 years) which I verified via county website and has a lien worth about $5K according to him.

If you are going to manage property yourself verify with an attorney that you can do this with the home in an LLC.6)  talk to lenders now.