Man, just in 3 years if you have the tenant leave every time, even without the negative cashflow, that alone can cost you an additional 20 or 30k.

Your primary strategy should be to have the Contractor and all Subcontractors add you to their insurance policy as Additional Insured. 

In addition to these you can find information about appreciation.Many of the people recommending expensive properties are doing so because of appreciation.

Second, I'd connect with some local hosts in your area also in addition to Airdna.

In addition, condos tend to not appreciate as fast in value compared to single-family or multi-family homes. 

You want to make this clear that additional items need to be purchased by the guests so they are aware.

I rented out the additional bedrooms to friends and family, charging them well below market, and sold when it was time for my wife and I to start our own adventures.

Unless you're in a Class A Neighborhood like Palmer Woods, Indian Village, Sherwood, etc,. the additional rent probably won't support the cost to build:(More profitable to take the build funds and buy another property.DM us if you'd like to discuss more...

I rented out the additional bedrooms to friends and family, charging them well below market, and sold when it was time for my wife and I to start our own adventures.

In addition to having cashflow to add value and push equity, I still have had decent appreciation.