I'm not sure why not - one of the great parts about real estate investing is that you can build a team around you for aspects you aren't as strong at or simply want to delegate to someone/expert and do the others yourself - look up "Core 4" for example - where you can have an agent, lender, manager, contractor all at once for your investments and can theoretically just let them do all the interactive work

Not sure you can discover a Concealed Eviction as this is the first I've heard of it.  

Ha, hosts anywhere could apply this to their region simply by changing a few verbs and nouns.

Not simply building wealth in additional to whatever else they have going on to support them.

Based on your post, it's probably best for you to simply not invest in Cook County for your own peace of mind.Sure, any tenant could stop paying rent and that risk is never zero.

(Hands-off or hands-on.)I like STRs as a way to make money while you wait for a property to gain value, but at least for us, cash flow is simply the icing.

@Michael Klinger  As others posted, SoFi and Discover personal loans are good options and I've used them in the past.  2-3 business days from application to funds in my checking account. 

It is a sure thing that you will have success simply based on your introspection!

.- If you're going after a seller finance deal I think once you understand what it will take to get to a finished state its simply a matter of aligning your needs as far as short term cashflow with the current rents/situation, with the net number the seller needs after the refinance.  

The real estate landscape is always evolving, presenting new opportunities to discover.