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.  

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.

I have a little inbound marketing going with FB combined with whatever my realtor is doing (mostly MLS syndication, I believe) and was wondering if anyone else has had luck doing outbound marketing and sales to investment companies and other fiduciaries?

The style of the house is somewhat modern-ish, so I would try to go from those cues. 

We are spoilt here in the US with large modern homes.

Any one of those or all three combined can make a property worth acquiring.

I don't know about the modern greys.

For 2018-2025, however, the TCJA limits itemized deductions for personal state and local property and income taxes to a combined total of only $10,000 ($5,000 for those who use married filing separate status).

My lease is a combination of the BP Connecticut lease, the standard lease template for my region and a few personal touches.