Yes you're right much better if they have an app

You have to earn some stripes through unfortunate situations like that to be a better investor.

You would do better to look at another market, and then take the profit of that vacation home to rent a STR in Orlando on vacation. 

Is there a better way to do this or am I sounding like I know what I’m talking about?

In this case, it was better than MTR'ing the property

The more the better!

Fantastic idea and even better deal if we can find a seller willing to cooperate.

I will research Catalyst to get a better idea of the services.

Hell hath no fury like a scorned tenant with nothing to lose :)Generally our clients are finding that SF rentals are actually selling better and more quickly when vacant. 

@Kristin Vegas - If you are buying in Chicago proper, be sure to become familiar with the landlord tenant ordinance which is specific to the city. https://www.chicago.gov/city/en/depts/doh/provdrs/landlords/...There is a good stock of multifamily housing just west of the city if you are looking for a more suburban feel with better schools and policing while still being able to get to the Chicago city center within 15-20 minutes.