As a broker, you’ve already got a strong foundation, which will give you an edge in finding and structuring great deals.Since you're in Chicago, have you considered house hacking as a starting point?

Quote from @Sarah Hartstein: Hello everyone, I am brand new to this website and looking forward to gaining some extra insights on property within the US and beyond ;) I started as a part-time Realtor with Keller Williams in Santa Barbara, California, however domestic sales never really “tooted my horn.”

Should we start LLC? 

My thoughts - this is a GOOD start.

And if this represented my total portfolio, it would be like starting over.  

This is definitely a good place to start and to network with people in the market you are looking to invest in.  

Live under your means and start thinking about investing in Real Estate.In your position the thought of finding a duplex to house hack, live in one side and rent the other. 

Then once you know how you will get the deals, that is where the fun starts..

You begin depreciating $200k over 27.5 years, starting from 2023.You do a major $50k rehab in 2030.

Theres one I think its by Brandon Turner that is called rent to retirement. when I was starting out I read one that was called one property a year that resonated with me.