If you have a short term rental, you need at least one tax return reflecting the income on schedule E for at least some portion of the previous year. 

I also offered that, as long as she pays July rent in full, I will refund any pro-rated unused portion on her move-out day if she moves out before July 31st. 

Does S8 allow it and or how does that impact the renter, does their portion also increase? 

The bottom line is you will be the only one who has any vested interest in the former owner delivering on the promise to be out in 30 days unless you hold a good portion of sale proceeds in escrow until the seller is out and the home is in broom swept condition.

And a good deal of properties that have HOAs/ Condos/ ect.....still technically own a prorated portion of land and still get alllocated. 

I have a couple agents working for me trying to find stuff off MLS but a good portion, like you all have said, are either in horrible neighborhoods or are just crazy prices contrary to what rent is going for.

If I am doing this should I just start with some portion of Private money so I don’t have to pay title company twice?  

When you hit 50+ it becomes a noticeable portion.

We secured grants for many of these developments and the loans we secured were cash flow loans, meaning that we would repay a certain portion of year end cash flow.

As relationships are vital in this community, I’m looking to introduce myself here and see ways to connect to other investors in Chicago.