When my wife and I started out we new we wanted to invest but did not know how to, we took action and unfortunately found a family friend realtor (amazing learning experience) then we found bigger pockets. 

Where in the Chicago area do you invest?

I personally invest in NC and it is very landlord friendly and business friendly. 

. $500 is probably cheap money for the upgrade.

At the end of the day; you need more money to do something like this.MAX LTV on new builds is 80% LTC, Meaning if the build is $550,000 and Land is XAdd ($550,000 + x ) * .8 = LOAN AMOUNTYou would need to come in with MINIMUM 20% of the cost in addition to closing costs and reserves, $80,000 is not going to cut it for this project.

My next goal is to invest in a multi family property with a partner.Welcome to BP!

Over the years the only place I have lost money is the stock market.

I''ve only heard of ones existing who work on large constructions projects, not small single family home investment properties. 

I’m just getting started in real estate investing and am looking to acquire my first investment property.I’d love to connect with like-minded investors, lenders, and mentors who can share insights or personal journey.

I wouldn't recommend an ADU and take that money and invest it where you can pull capital out faster. you can do much better.