Talk to your CPA and Lawyer, Get the right tax advise for you and your short term and long term plans, and talk to multiple lawyers to get familiar with all the different structures.

They are quite aggressive in the Keys in enforcing the No short term rentals without the proper license, which is difficult to get.

Long story short they’ll probably still be around

My partner and I grew our portfolio to 5 properties within a few short years, but he never felt that the benefits of real estate investing outweighed the risks... despite the profits we made while downsizing. 

The more home visits you can accumulate in a short period of time the faster you will get comfortable.

The townhouse is a short drive to the future Raiders practice facility and supposedly the site of various new construction projects (malls, high rise condos, etc.).  3. 

Your exit strategy could be to rent it out,  but you would need to evaluate weather a property would cash flow as a rental (either short term or long term).We live in Seattle and had considered buying.  

So I guess my only hope is that I can convince them to add me as a third party and try and negotiate a short sale?

I know the useful life left on the roof is short, so I am hoping there is some negotiating around that.

I would think the involvement of any such association could be a hindrance to running a legal short term rental since so many restrict them.