You need to have some strict verbiage in your listing and your RA about this.

Are your requirements too strict?

Gold Beach has strict STR rules but outside city limits in the county there is very strong oceanfront value that can get also obtain a vacation rental permit, listings there do typically go pending quite quickly. 

As the department of buildings has very strict codes of use.

DSCR loans offer alternatives for DTI/income and employment, but generally still have strict personal credit requirements. 

I did walk away from this exact property but it was good practice I think for me and I will be looking into some more in the coming weeks.My next question is property management for something that strictly does emergency calls where I can not be present?

Generally any hold of more than a year is considered routinely safe.

Although it's not a strict rule, this can serve as a useful guide.A frequent goal for house hacking is to have the rental revenue from the extra units completely cover your mortgage payment.

Just to add on to what @John Warren and @Sarita Scherpereel said security deposit rules in Chicago are very very strict.

Mid-Stay Rentals (MTR) offer steady money with leases from 1 to 6 months but with okay cash chances and strict rules.