As a general rule of thumb most municipalities expect for the applicant to demonstrate hardship.

I understand that if you live in a state that does not have a state income tax - you won't have any state tax liability, but based on $110K income, you would be in a 24% federal tax bracket...Distributions from an IRA or Roth conversion would be considered ordinary income and subject to ordinary income tax; capital gain tax is not applicable here, so I'm not sure why you are bringing it up... 

You need to research/know the rules, laws and regulations (including HOA if applicable), like you'd do in any US city.

Maybe the landlord isn't responding because they don't see the applicant as meeting their criteria. 

It's a really sexy application on webinar, but even for the "Get It Now" price may not be worth it if you can't shut it off in a timely manner.  

I have never done an application for a rental because they are so happy to find someone who is going to help them with their good location, but needs just a little work, property.

You will need to submit a detailed permit application to the Chicago Department of Building.

Another thing to consider is are you basing the 3x rent on her initial application? 

These are decisions to can make to subtly change the applicants to get and how long you keep a good tenant thereby affecting your vacancy/turnover costs. 5.

Do I list the foreign mortgage on my application?