I like following stock markets, cryptocurrency markets and love to travel. 

You might find that the stock market makes you more money with less work (seems you are trying to minimize your involvement w/ the rentals). 

Chicago is losing housing stock at an alarming rate. 

With a HELOC being around 9% I'd probably be paying more in interest than the money would make in the stock market.

After finding outlets and switches placed in bad spots and plumbers who wanted to argue about the use of Pex manifolds my subsequent projects I literally would pound all the electrical boxes and label what they were for and buy all the the materials myself. 

You're picking a great time to start investing, the area is becoming a hot spot for investors. 

You can point out spots like nail holes where they hung pictures, dirty spots in the apartment needing cleaning, blown outlets they are overusing, etc.

Small, local banks and credit unions always have connection issues no matter the software...Having been associated with Stessa/Roofstock for many years now, I can say that this is spot on.

It happens sometimes, but usually you can spot it if you do your diligence and call the employer and previous landlord etc.

I was able to rent the garage to a seasoned electrician running his business through there only coming in and out to stock his truck once per day.I hope to be able to convert the second floor into an ADU as soon as Feb 2nd rolls around.