Fortune Builders has substance and I met interesting thinkers in the 3 day workshop as well which only cost $197. 

I, personally, always think it's a dangerous assumption to assume "bad management" or that the owner is selling because "they want out". 

The most dangerous thing you can do with cash flow is "play with tight margins"   like purchasing a house for 275k while the rent is below  aprox 2900$/m and thats roughly ... as i would never risk that much money on high end rental because they fluctuate too much  (nearby developments, markets going up and down, someone decided to raise taxes again ...etc)cuz just imagine ...today  you are going to make 2700/m from 275k  which roughly means your cash flow is going to be ... $150-200 bucks a month after everything ( PM, taxes, P&I, some other Opex and Capex)  and dont quote me on that exact number  its just meant to show how tight of a margin you will get.   

You can also ask the seller to renegotiate the price, but he isn't obligated to do so.Cash deals don't require an appraisal because there's no lender involved, but you can ask for and pay for one for your own purposes.BTW, this is the textbook definition of the dangers of buying the biggest, nicest, fanciest, and priciest house on the block.

Excessive upfront fees are dangerous for the borrower.

In terms of numbers how close would Chicago city properties come to the to the 2% and 50% rules.I have not moved to Chicago so I'm still unsure of the dangerous neighborhoods.

I feel like a phone call might have a lot more substance, and people would remember who I am.

The dangerous double whammy.   

[As a rule of thumb, investment properties are in danger of negative cash flow if rents gross below 1%/m!]

Bidding on properties you've never seen in a place you do not live is dangerous unless you have a great feel for the area, have invested here already, or have lived here recently.