You should definitely buy a property and give/rent out rooms to the homeless and disadvantaged.

Security deposit laws in Chicago are disadvantageous to landlords anyways.

Quote from @Hector Espinosa: Hi,I'm negotiating a seller financing deal which may be my first one and would like to ask for some advise about and what are advantages and disadvantages about seller financing deals.These are the seller financing terms:House Price: $330,000.00 USD​ (Sellers still owe ~$301,000 USD)Down Payment: 5% = $16,500 USD​Loan Amount: $313, 500​ (Monthly payments will be amortized as a 30 years loan​)Interest Rate: 4.531%Balloon Loan Term: 5 YearsMonthly Payment (P&I): $1,594.24​Closing Costs:  ~$3300 ​Zip Code: 74105Observations:       * HVAC requires an update but pending to inspection (replacing with a new one will cost ~$10,000 - $15,000 USD )     * Expected Rent Income: $2,000- $2,300 but this is has been really complicated to get a good estimate because is all over the place in the different sites I have checked

A disadvantage to this type of investment is that it's likely your MOIC (Multiple of Invested Capital) will be lower than that of a common equity investment. 

you have an easy house hack opportunity that does not have the disadvantages of an ADU.  

We would try to find solutions for issues as best as possible as long as there wasn't any cost or disadvantage to the utility.

This put us in a significant disadvantage on selling, buyer has to have 20% down and buyer needs to use a Non QM lender too instead of a standard back or broker...

The worst MF is probably the small 5-12 unit space: you have all the disadvantages of MF, without the synergies.

Quote from @Hector Espinosa: Hi All,I would like to hear your comments about the following property, which I think, based on the analysis I made, seems to a be a potential good investment:* Purchase Price: $98,000* Monthly Cash Flow: $310* Annual Cash Flow: $3731* CoC ROI: 15.86%* 5-year annualized return: 15.35% (with a profit if sold of $25K)Also, what are some of the disadvantages of buying old houses? 

They still need to have license.The only disadvantage that I'm aware of is that if the insurance goes bankrupt then the state would not step in and pay you if the state has any money left.