Feel free to reach out, and I can share some recommendations based on your project

Should he be exposed to all liabilities that comes with it such as lawsuit, history of insurance claims(I believe insurance have a data base of past claims that can affect future coverage), credit and what not at an early age? 

I suggest running an analysis and just sharing it here on BP.I am also happy to hop on a call and point you in the right direction based on some of my experiences- no matter what, keep at it...this stuff takes time.If you get a deal here in Chicago and need to partner up, I am your guy!

We don't bait and switch, we work deals based on actual details of the client's specific deal.

What kind of database should I use to keep track of my leads and client base?

So @Mike S. is providing the perfect solution for you. 

In a perfect world that’s how I would start since it would be a lot easier than buying a home but I’m sure there’s some things I’m overseeing.

SO expect to pay a premium based on what the potential value of the building can be once maximized and stabilized.

Good luck to you and I hope you achieve all your goals in lif I actually understand perfectly.  

I'm currently renovating my rear unit and it has the perfect layout to split into 2 units by adding a wall and an additional front door.