@Mallikarjun Reddy Pateel - piggybacking off of @Jake Fugman's comment, management will be 8-10% on paper for something like this, and these Chicago high caps also tend to have higher turnover.

While someone may look good on paper, they may be the biggest PITA in person. 

Lots of people get surprised when buying lower priced rentals in the south and the midwest when they do their taxes and those "on paper numbers" are not reality when the banks look at them. 

Seller is also willing to do any additional paper work needed to get this sorted out.

I was cold calling like a machine, I tried CRM but couldn't get it to work for my brute brain (Eventually I found close, and I could never operate again without it) so I used pen and paper. 

The borrower shows up at the closing table and signs the papers, pays the closing costs and whatever was required for down payment and then the loan funds. 

For cleaners - use TurnoverBnb or Properly AppI use the Thumbtack app to find vendors (plumbers, electricians, handymen, wall paperers, etc)Definitely make use of a program like Hospitable or OwnerRez to make conversations with guests easier and automated.Outside cameras are a must and asking for photos from your housekeeping staff after each clean is vital.

Is there any benefit of "collecting" rent on paper up to this maximum loss threshold or would it be better to report the maximum loss?  

If you are not going to go to college, I would then get in one of the trade schools and get licensed and work for 2-3 years to get up to your master license in Electric or Plumbing.If you plan to go to college, then you might also spend some time during the school year getting your real estate license...and working on the paper side of the business while you go to school...so that might be 2-3 summers and 2-3 years during school. 

If an owner says they are willing to hold paper it means they are experienced and will do seller financing.