Last, but not least I'd suggest speaking with a securities attorney in general on the investors' topic to ensure full compliance with the laws. 

If the borrower’s credit file includes complete and accurate information to ensure the validity of the credit score, the lender does not need to further evaluate the borrower’s creditworthiness.https://www.fanniemae.com/content/guide/selling/b3...If you have your credit pulled for a mortgage and look at a copy of the report, you will see that those versions are listed on the report.

Great strategy...but, you need the proper docs, and those docs MUST separate the lease from the option. 

PM's need to be trained/guided to work properly with your style and expectations of doing things, or they will get feral just like anyone else.

Do some research on similar homes in your area and first make sure that it's properly priced.

You may even want to market to obituaries if you can figure out the proper decorum.Good luck.

To refer to the map you posted.67th to 71st (Jackson Park Highlands) is decent.71st to 75th - South Shore "proper" Noticeable difference.

If it was his property manager, it was his responsibility to ensure that he was providing you with the current leases, especially if he knows his PM does not check with him before signing leases.

So if your CPA is preparing your tax return, they are not necessarily ensuring you are paying the bare minimum taxes. 

I follow all local laws, have all the proper permits in place, and pay all the proper taxes on time or early ever month.When I purchase my next STR in Nashville I will continue to follow all local laws, proper permits, and pay all the proper taxes.