Who paid the $20,000 original cost of the home? 

They can provide you with a cost estimate and help you plan out the build from start to finish.

The property hasn’t pulled in a lot to cover the cost but for safety I can manage fixing some within budget. 

On paper this may look like an obvious solution, however, in practice it can cause more challenges (cost) than it saves for most situations.

I did not do this with two partnerships and one ended in a lawsuit and the other cost me tens of thousands of dollars.

For cost effectiveness we are using Citizens but he has several options to choose from.

Get with a good agent who understands short term rentals because the more of these you do then you can scale the insurance under a Business Owner Provider Policy (BOP) and then you don't end up with a dozen individual policies out there for each property that cost you a fortune.

But that is rare in today's market with high cost to build

The cost in IC is a significant barrier to entry, however and the ROI is lower, in general. 

Negative CF is an added cost that defeats the purpose of buying RE.