I’m planning on purchasing a few OOS properties to supplement Ca properties.

You can use cash generated from the losses if any to supplement your 1031 purchase.  

My older brother, who is currently flipping his first home in Philadelphia, enlightened me on the possibility of real estate as not only a supplemental income but more so a way out of my house via house hacking.  

Then, supplement with your own research.BPO's are beyond worthless.

My husband and I have a goal to purchase some buy and hold units to supplement retirement in 10 years.  

Unless Chicago experiences similar appreciation as LA, which I don't see based on pre-recession vs. post-recession median home sales price numbers, the implementation of a Rent Stabilization Ordinance will discourage investment from buy-and-hold investors, who will start to see a squeeze on cashflow (restricted rents w/rising property taxes) supplemented by sub-par appreciation gains.

I'm definitely going to stay on bigger pockets because this is a very powerful and free tool to have, but I'm also looking to supplement this really awesome tool with other tools that are out there.  

I'm ultimately looking for a way to supplement and eventually take over my salary from my "day-job."

I work as a Construction Lead on a project team, in the animal nutrition industry, doing R & D for new products and continuous improvement. 

I have my bachelors in nutrition and am currently pursuing a degree in public health.