To prevent this from happening I combine the payments and lease signing in one visit.  

Combine that with tenants that don't take care of the place and have high turn over and the numbers just can't work.

Having inquiries rarely negatively affects your scores.

This is combined with money coming in over time (over the term) of the contract and ideally, it covers more than anything they pay out monthly if they have a loan. 

I always update my units, so I rarely get calls.

The rent is due by the 1st but she rarely pays until the 10th as she can get away with that in CT.

The south side of Chicago is a very large geographically (South side is as large as the north and west sides combined) so it is unlikely that one property management company will cover the whole south side.  

It is rare that any SFH will cash flow without a secondary suite.

There are a few stipulations that tend to be a bit tougher to qualify for than a standard HELOC, but if you can get it, it is as advertised.I have a local bank in Omaha that has two of my rentals combined on one First Lien HELOC, but they don't work out of state.

For all these rehabs I have done cash of some form ie. private money, hard money, my own money and combination of two or three of these.