On the journey, I once sold properties that were 30 minutes away as being too far, and also managed some properties that were 200 miles away. 

I am from the Hagerstown, MD area and was looking at a few potential investment properties in Cumberland.

The LLC sells the subject property and buys, for example, 3 replacement properties in a 1031 exchange. 

Foundations actually don't come up that much in Chicago.... so many awesome brick properties.

As for the property you posted, that is a great area. 

Keep the property IMO.

Until now I've focused on distressed single-family and small multi-family properties for rehab into rentals (BRRRR).

Whether it’s helping a seller get their property in better shape for showings, structuring a deal that works for both parties, or connecting the right people, there’s always a way to add value.

Keep in mind that inexpensive properties are inexpensive because they are less desirable properties in less desirable areas and attract less desirable tenants.

As you progress your bookkeeping business, you'll likely want to learn how to export statements from a variety of property management platforms, as investor books are housed in bank accounts, spreadsheets, and a variety of property management and accounting software!