a) Get a pre-approval from ONE of the lenders and use it to put in offers.

You have to put in the work to be successful at this!! 

If it were one of my tenants I would put in enough window units to keep the house comfortable.

Hey @Denise Crudup - JW is right you just need to put in for a zoning certificate here in Chicago.Here is a link to the PDF: https://www.chicago.gov/content/dam/city/depts/zlup/general/...Maybe also worth taking a look at the Chicago zoning map just to double check your current zoning:  https://gisapps.chicago.gov/ZoningMapWeb/?

But if you want to put in an offer, I'd love to help you, I'm probably in the single best position to get you as buyer the best price.

I agree with the other sentiments that this law seems reasonable and that it will weed out the investors not willing to go through the processes, making it better for investors who are willing to put in more effort. 

Put in new fixtures and flooring.

I am almost ready to put in an offer for my first STR in Big Bear.

A faux wood look with an almost black or dark grey siding would help distract the eye.But, all of this costs money, and typically beyond some cleanup and fresh paint, on a rental is the best bang for your buck.

My question to you is what systems have you put in place that has helped with your growth.