Can they perform on their terms?

The problem with that is that I spoke with a bunch of Real Estate Attorneys that assured me they can and do perform the same services (contract negotiations, advising, etc…) and they do it for a fixed hourly rate as opposed to an equity stake.

In your opinion, what amount would you have to have paid out for someone else to perform the work you did?  

You are definitely negative cash flow.Yes, I would consider selling it and moving the money to a property that performs better.

Focus on the overall cashflow because maybe for you it only takes 10 properties to retire and for others maybe 20 some might need 5 it all depends on how their portfolio is performing. 

However, past performance of appreciation is not necessarily indicative of future gains due to variables within each market.

What are the top amenities in the area for the high performing STRs?

I’ve encountered managers who were fantastic in most areas but lacked in one or two key traits, and that was enough to impact the performance of the property.

Also @Tim Phillips something to be aware of in FL, all condos older than 30 years and taller than 3 stories are required to have a "Structural Integrity Reserve Study" performed before the end of this year.

They generally do not do this because either they are not aware of the changes or the loan is seasoned and performing so they are deliberately turning a blind eye.