Congrats on your cash-flowing property in Chicago! 

Specifically, I would encourage you to continue to seek local opportunities for equity growth as well as seeking out-of-state or upstate opportunities for cash-flow (i.e.

So guess which route I started with? 

I feel the investor is off to a great start.

When you’re just starting out, the numbers can feel tight because a lot of the cash flow gets eaten up by repairs, vacancies, and other unexpected expenses.

It's the safest way to start and it's a guaranteed profit when you get the right deal!

My business partner owns a roofing company but has weak credit and more limited cash flow.An LLC is a common choice for partnerships since it protects personal assets and simplifies tax management.

That will start to help form your strategy.  

In the past, I cashed out my 401K(Paid income tax + Penalty).

Leverage your existing equity to invest in smaller properties, such as a mixed-use or retail space, to gain experience and cash flow.