Neither tenant has leases however not sure if eviction is an option Chicago has unique set of rules due to COVID and not forcing any eviction until July 25th.

I am starting to explore other options and the obvious choice is Philly.

If you want to explore out-of-state, you want to read David Greene's book and see if it could work for you.

Seattle Metro has a unique protective bubble around it, not to be confused with a real estate bubble.

There are certainly well explored downsides to STRs, but what you're highlighting here is the trump card in this very moment!  

This is a unique market, but there are definitely opportunities out there for you!

Explore SBA loans which will allow you to purchase property with 10% down and much more favorable rates than commercial loan.

It's very easy for me to look at all the things I don't have (access to bank financing, many years of experience, money to burn, etc.) but I'm shifting my focus to the unique things I do have.I'm able to fly for free thanks to a family member who works for a major airline.

I am new to real estate investing and interested in exploring this strategy. 

I live in the Seattle area but am exploring options in the midwest and south to invest in.