Also, key Due Diligence items.  

Hello and thank you for responding/helping me to get a better idea of moving forward.So, Yes, I would likely be able to move my main business to a rental location and preserve most of my income.

I'd start with option 1 and remind her she's already behind on rent and you're giving her the option to move out without the need for an eviction.

There is a ton of new construction because developers are having to start moving away from the beach areas.

We just moved out and are renting it long term and making around $400/month.

As long as you like your job and/or industry and could do it for the next 15 years, what you are doing would work perfect for your plan.As you gain experience, maybe you can move into more units per purchase or start to BRRRR.

That may be, but Chicago and Cook county are EXTREMELY tenant-friendly hell holes as far as landlords are concerned.Don’t move to a place because of its laws.

I've done my research and feel that this is slightly below market price.I plan to move into downstairs unit once I can get current tenants out. 

I've been told Cash for keys is a good method but how do you go about doing that?

It will be great if I can remotely set up entry key code for open house or new tenenant.