Think rent growth in a city like Seattle or Boston, but in Chicago, you can actually afford to get into the game.

In these areas, you will generally not cash flow that well for the first few years, but years later (like me now), I can retire off the profit that I make from these same properties.Ultimately, this is how I chose to play the game and it is not the perfect game for everyone.  

I own 4 long term rentals in Memphis, and I've found it to be a great city to invest in, so I'd really encourage you to find some good properties and get into the game!

Maybe I was too ambitious by expecting to get a solid property in a solid area for $100k below assessment with no competition... but man, I am going to have to up my game! 

Hi Late to the game here.

I am choosing to NOT use a RE agent as the last 3 i tried were a nightmare and just tried to “just get me in to the game” with any cost and they clearly had no clue about lending.

You might not start in it right away, as you may need capital and experience, but you will at least have a better vision for your end game.

I am looking to learn what is the best way to leverage that through LLCs to get into the multi family or long term rental investment game. 

In today's market that is a game changer.  

I would just say the biggest red flag here is "anything sounding too good to be true" - whether thats a hard money interest rate well below market, or 100% "no skin in the game" financing, etc. - those are the biggest red flags here IMO