I have noticed whilst driving around a small ground floor apartment, it appears to be unoccupied, blinds are closed and i can see mail piling up between the glass door panel and the curtain over the door.

The first couple years I bought blind without doing a title search and i made mistakes and it cost me money.

Im a phoenix agent and investor whos been asked this as well.People that are pricing their current str's or underwriting new str's based on 2020-2022 performance are leading themselves blind.

Blindly looking for positive cash flow without considering all the other angles of an investment opportunity is just as wrong as looking for rapidly appreciating markets without regard to any other element.

Definitely not something to jump into blindly.

Otherwise it might very well be the blind leading the blind....lol.  

I'd say I'm at that point where I'm still learning, but am looking to make that transition to learning by doing, while not going into it blindly. 

Any pointers - I have blind spots and likely do not even know all the questions to ask you!

Also, don't blindly believe the stories the son tells you.

Chicago is a city of neighborhoods.Especially on the South Side, things can change by just a matter of one block to the next.Out of town investors I find get blinded by high pro forma numbers that in reality never exists in many neighborhoods here.