This self claimed "Drug Addict to CEO" doesn't pass the sniff test in my opinion.

There will always be posters who come out of the woodwork who claim to be able to beat terms or meet borrowing expectations.

How would an umbrella policy protect against a security deposit related claim?

They claim it is a triplex (two regular units and an "efficiency unit".

I'm thinking about just taking him to small claims court, can that be done? 

Do I go about doing this by performing a Quit Claim Deed?

A sophisticated investor will also typically ask for the entire claimed track record and then run it through the wringer.

We are now suing them in TX small claims court as the security deposit was not enough to cover the 2 - 3 months rent after they trashed the house. 

Also, most Umbrella Policies only pay out if your underlying policy pays out, and the underlying policy will do everything they can to find an exclusion or that you were negligent (which you probably were) in the cause of action to get out of paying the claim.

Hey could also claim he was mentally ill, not of the right mindset, he could argue he did not sign the agreement someone signed it for him.