Just reading that $90K figure raised a red flag for me. 

As long as their credit score comes back clean, and they haven't missed a payment, I don't see any red flags.      1) Increase late fee, or even better--  set up the lease where they get a discount if paid via the first.    2) Require a co-signer3) Up the security deposit

Then the report is delivered to the AMC's automatic review, and if no red flags are found the report goes to a reviewer.

They have no customer support (repeated messages weren't responded to in months) and they flag the term "real estate".

He  explained that this  maneuver would draw  red  flags  from FHA  and that this  is not possible.

Call for sure to verify, but I would not raise the red flag for sure just yet. 

Major red flag when people ask to pay so much upfront.. why in the world would they want to get rid of that much $$.. unless they know they will prob leave after 6 months."

Craigslist does have a very sensitive reporting system, though, so if you get one or two people flagging an ad it'll likely be pulled (and make posting other ads difficult for the next few days).Sometimes I love Craigslist when it finds me a buyer and other times I don't love it when it gives me issues similar to what you're experiencing.

Also, you have to file the claim through Airbnb, not the carrier that is actually underwriting the policy. 

For example: Someone decides to sue me because I injured them during a flag football game (this is completely fictitious FYI).In this scenario, my worry is that someone might try to sue me, realize that I own multiple real estate properties, and try to essentially drain all of my money and force me to sell said properties.What is the best way to mitigate this?