I already have an umbrella policy so not sure if upping that premium or moving it into any sort of trust/land trust or something else would be a smart move. 

I would think Airbnb or VRBO would have some stats or something you could use to gauge the market.Set up some key word alerts for there as well.

Some things I did to streamline some of that is pay some of the expenses in batches if you can't or unwilling to automate.Maybe what you need to do is look at streamlining your own process. 

Is this something worth pursuing? 

Houses that need less than less than $30,000 worth work so not something that is not too old.I am trying to do the same model as Dr.

That could be something else to consider

And if so, what is the cost and prospect for collecting something, certainly not all, but something.My thinking is that if it shows up on their credit, it may hamper employment, car purchases, rental applications, education funding, etc and at some point they would need to pay me to go forward with some major life steps over the next 10 years.

Don't be afraid to tear out something and completely redo instead of patching.

Two different things unless Chicago has something special.

I wouldn't generalize this to something being exactly "wrong with investors these days".