Structuring the deal properly (like through a land trust) can reduce this risk.Your best bet is to connect with an Illinois investor who has successfully done sub-to deals or find a local real estate attorney who specializes in creative finance.

Your best bet would be to have a FurnishedFinder account and used their "stats" page. 

(And then any state implications)Given this isn't pennies we're talking about- working with a qualified professional to help mitigate the tax would be your best bet. 

Probably your best bet will be to do a joint venture with an equity partner.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

Your making a bet on them, that they can operate there business well and thus, will be good tenants. 

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

Office space is gutsy at this time with many companies working remotely, maybe part of your investment was to bet that people will be coming back to work in person.  

The duplication is mentioned by name by Santarelli and on the slide also included the following entities: Linens and Things, Stein Mart, Modell’s Sporting Goods, and RadioShack (37:52).

If they do, your best bet is a local community bank that funds these types of properties.Another option is a private lender but that money will be pretty expensive, as mentioned 10%  +