Free beer, pizza & food on Saturday night, since there is no longer any 'squatting' law enforced.I wonder how fast your non-paying tenant would move in those circumstances?  

Been putting it off but don’t want to be neglecting anymore.

In your current circumstances, the only logical option would be to get a cosigner.

And, if none of the above protect in that circumstance, is E&O readily available to an LLC that holds property and/or remodels?

According to a Facebook discussion, the owner stated that the tenant would not qualify (felon /poor credit) under normal circumstances and only gave this guy a chance because he worked for one of his subcontractors.   

God sent circumstances allowed my wife and I the opportunity and ability to rent out our home to a great tenant.

$2,100 Costs Gross Income CAP RATE 10.99% 9% YES $998.77 $25,200.00 CACROI 5.42% 10% NO maintenance $ 420.00 20.0% break even point in months 102 60 NO vacancy $ 210.00 10% NOI $ 471.23 $500 NO down payment $ 46,545.00 29% Tax liability $ (181.65) $ - YES Fees $ 1,605.00 1.0% Annual Net Income $ 5,700.13 Cost of Capital Improvements $ 56,150.00 Monthly Profit $ 471.23 TAX Money REVERSE VALUE Net Income $ 21,501.25 $238,902.80 Depreciation Expense $ 5,836.36 Projected Taxable Income $ (181.65) Item Cost Tax rate 1.81% furnace $ 5,000.00 Estimate Mortgage AC x2 $ 10,000.00 Interest rate 4.00% Archectect $ 6,000.00 Payment $690.54 Chimney $ 2,200.00 Period in years 20 Radon $ 850.00 PMI $ - Hot water heater $ 1,500.00 Taxes $ 242.09 Cut Floor Joists $ 600.00 Insurance $ 66.14 First floor remodel $ 30,000.00 Total $998.77 Utilities Deal 3#3 is a neglected duplex in a prime location. rents havent been raised in over a decade and are less than half market rents.Its been haphazardly patched up through the years cosmetically but the big stuff looks fine. will need new kitchen cabinets, appliances, paint, flooring, etcwill also need the current tenants to move out.

As I'm trying to help my family Move out of their dingy mold-infested rental that their current landlord is neglecting, as well as kicking off my Real Estate Investing portfolio.Just checking to see the viability of such a strategy and getting some more experienced eyes on this plan I'm concocting. 

Under normal circumstances, Chicago is tenant friendly, but in the pandemic you are walking on egg shells. 

They neglected the possibility of regulation, and they neglected the possibility of an oversupply depressing prices.