HI Pierre,As long as you can obtain the necessary margin between rental income and your costs to achieve your desired return then it could make sense.

Nothing abnormal with the negotiation strategy using 2-T How did you finance this deal?

My concern is if damage continues to happen I'm not sure if the security deposit will cover all the damages and am unsure how successful I would be in obtaining any additional money from the tenants to cover damages in excess of the security deposit.

@Peter T.

To me that might be a win-win too if they are not strong franchisers or business people.I really don;t know much about them other than I am in Texas. 

With regards to the response that I obtained from a member of the Planning and Permitting Division and the city not "permitting" STR ,  my lawyer's response went something like that - "permitting" as if "issuing a permit" or "allowing."

I firmly believe that type of product you provide is also a direct reflection of the type of tenant you will obtain.  

No sh*t sherlock!

That will drive far more traffic than anything a FSBO could obtain on classifieds, newspapers, social media, etc.  

I've read a bit on how its harder to obtain financing as a 1099 employee vs a W2 and how lenders typically want to see at least 2 years of earnings before they consider lending you out a loan.