This definitely helps though.

Any help would be greatly appreciated.

The cash flow from the rental will help your lendability. 

The cash out does depend on a few things like neighborhood appreciation with strong sales or renovate and refinance on the ARV (After renovation value).When you buy a 2-4 unit you get to use the rents of the other doors as income to help you qualify.

I like to share this story as a cautionary tale and while nobody has a crystal ball and can predict the future, understanding the end goal can  help investors understand  whether they invested in a market that can reap the true benefits of SFH rental ownership or perhaps point them in that direction. 

Hey @Lisa H.Checking AirBNB and VRBO to see what other STRs are bringing in will help.

If you ever need a hand with funding, I’d be happy to discuss hard money options to help you reach your goals.

There are a whole lot of factors and differences among the options, even among lenders that fall under the "private lending" umbrellaSharing an article published last year that maybe can help and provide some more insights:https://www.biggerpockets.com/blog/dscr-loans-terms-to-know

Just have 1 unit /condo in chicago loop, that is now available for renting.Posted on Zillow , total of 6 applicants. 2 very interested parties.What tool/website should I use to do a comprehensive background check? 

I am interested in making connections, learning new ideas on how to improve our properties, offering help where I can, and of course, finding more properties.