A little bit about me; Prior to the market crash in 2008 I had experienced some success investing in real estate but , like most of my RE peers at the time, I was painfully ill prepared for the market downturn.

However, he is in quite poor physical health for a 60 year old man (very overweight), so I've emphasized to him that this area is even more important than having cashflow.

@Russell Brazil thanks for helping the pain!!

We filled it in, was a pain to do but its gone now!

How much pain will I get with having say 20 units (just theoretically speaking) located in several places in the city vs 20 units in one residential complex.

Ryan,I feel your pain my man!

There is absolutely no debate that if you have 10 rentals, all belonging to the same asset class, that were the class suddenly to go to hell in a hand basket you aren't going to be in for some pain---major pain.

He can get sued for fraud if he knowingly covers a health or safety issue....not sure what the laws are in Illinois, but Alabama is a buyer beware state, so it may be hard to actually win - but sounds like the buyers would have a pretty good case.

Recently, due to some health problems and other issues, it looks like I will need to change careers.  

The Hero Loan Program as I know, helps anyone who is an education or health professional with purchasing a home.