Right now I house hack, but am looking to properly get in the game by end of next year, so I'm trying to be prepared.

Its a numbers game. 

I've found the same when using pricing tools, but I've heard from others that it's been a game changer for their business...

Why don't you share your info and your background and how many deals you have done in the land game.

Oops, game over, you lost.

I currently house hack in Chicago, however, going from that to STRs where I cannot self manage is a different ball game and just wanting to pick peoples brains who are doing what I'm interested in doing.  

They have more skin in the game then you do.Make sure you get clear title.

I own a property management company and am looking to get into the investment game too and to meet people on a similar path.

Then you are 'in the game' so to speak.

Also, that is why I am looking at SFR compared to duplex etc, to keep the initial headaches simpler with just one tenant to manage