I get the desire to own outside of Chicago proper, but instead of going to another state altogether, why not invest in one of the burbs?

Just the other week I was giving a tour to a potential Canadian investor, and they were shocked at how quickly a street goes from mid/high-end to....well, not as desirable.

Choose the Right Property:When choosing a house to flip, search for properties in desirable neighborhoods that need structural or cosmetic improvements.

Still has lots of belongings (including a boat) in a large shed on the property... could imply intention to move back, or a desire to not have to deal with it and possible interest in having help getting rid of all this stuff3.

@James Wise gonna have to disagree with the "lie cheat steal" concept regarding residents.Any resident has the potential to be less than desirable.

From our experience, it is typically within a month of their desired move-in date.

While the property's location was desirable, it was evident that the house had been neglected for several years.

Single families are generally more desirable for tenants & you also get longer staying tenants most of the time. 

Lake side homes are more desirable for short term rentals in this area but not impossible to accomplish.

There are other ways to legally raise capital, however, they have some inherent disadvantages making them considerably less desirable for what you’re trying to do.