If you haven’t I might try just an aggressive servicing and see if that boosts performance. 15 years isn’t that long for a good system.

I get that sub2 and wraps and long term lease options all have risks, and they are not for the faint of heart or for broke RE people without resources (own credit and cash, private funds, jv partners, etc). 

I charged a $250 non-refundable holding fee that would be applied to the security deposit, but I was starting to feel nervous that tenant might have change of heart and then we would have to start all over searching for a new tenant.

@Teho Kim looks like that’s south of sacred heart/ old south side.

If you want to boost the return on the equity.

But otherwise, it's a great way to boost your rental numbers.

Purchase price: $143,000 Cash invested: $10,000 Sale price: $153,000 Lucrative vacation rental, Intracoastal fronting, dock and deep water boat access, resort vacation community in the heart of Palm Beach.

Not impossible, but the odds are stacked against you and often you are competing with extremely well qualified and experienced investors.I've been hearing for years that people have been just killing it in the short term rental space, but I'm a conservative investor at heart and while revenue is frequently higher, there are many additional expenses and often an exceptional amount of volatility just inherent with short duration stays. 

That holds a special value in many hearts...lol

You seem to have a great heart by the fact you even had this question.