It would be cheaper to establish and manage the structure without the middle holding company LLC, but I may be missing a big "gotcha" if a black swan event occurs.  

@Krystian Sosinski a black swan event is so named because you never saw it coming.

I use black magic marker and hand write all my signs.

But seriously, consider these scenarios as black and white (if your 'bad tenants' are simply just annoyances and you want to get rid of them legally):1.

We are replacing bedroom carpets (rest is hardwood), had to do some heavy duty scraping (travertine tile floor and the goobers that did the grout did not wipe the excess off the tile at all) and deep cleaning in the bathroom (tub was BLACK on the bottom!) 

@Eric Black Thanks for allowing me to bounce some ideas off of you!

@Ryan LaRocca You are not going to find a perfect answer because laws are never black and white, and often other less obvious parts of the law apply that you don't realize.

It doesn't make you look like a well established company that has experience processing billions in transactions.3) On the mobile website, the About | Buy | Sell | Invest | Videos | Contact black banner is missing from the top of the page.

If you were long, like a Hedge Fund owner I know, on Black Friday, you would have lost everything with the Margin Calls and had to shut down the Hedge Fund.

Pot calling the kettle black there, Jason?