The tenant moved in Back in 2006 and the previous owner proclaimed total ignorance and said he didn’t have the lease agreement anymore and never touched the security deposit, pointed fingers at KW that handled the lease for him.My tenant gets a lawyer that procures the full lease from 2006 and clearly states the money provided for security deposit and last months with ex landlords signature… the tenant is now also saying his money should have been in interest bearing escrow account providing statements to him all this time.The previous landlord clearly messed up and possibly doesn’t comprehend his own responsibilities.

I went to a seminar where they taught us how to approach lenders.

How would I approach the investor or how would I make sure they don't go behind my back and kick me out of the deal?

I already knew what he was saying as I follow lots of economists but there was something about his presentation that confirmed the path I am an on and I felt like he gave me permission to fully unlock an aggressive approach to acquiring property. 

Interesting approach!

It’s super easy to feel overwhelmed when you’re trying to teach yourself something and there’s a million different ways to approach it.

Any information on how I can approach this here in Chicago, would be extremely helpful.

There are a couple of ways you can get started in RE; the most common approach is house-hacking.

I think your househacking approach will be a great strategy in most areas.

Especially depending on your approach and if you're ok with appreciation and not cash flow (older houses will have maintenance and newer houses have hefty HOAs and MUDs).