So if the homeowner saves energy or goes on a long vacation, they still get charged 100%.

Start as a co-host and work under a vacation rental management company in the area to learn the ropes.

I hope you enjoy these books recommendations!

I have enjoyed Stessa's interface but unfortunately it is useless to me if I have constant bank connection issues. 

For most vacation rental areas, irresponsible people are not renting homes.

Reason why is because FDIC Bankers "Do Not" charge points on traditional programs like primary homes, standard investment purchase and refinance, Second home/vacation homes.Lenders, Brokers all charge points to meet their Loan officer compensation plan (commission).

Through the years he enjoyed positive cash flow with the last ten years cash flowing at about $17,500 annually.  

I’ve been coaching new investors for a while, and I always enjoy hearing about what brings people to real estate.

But if you have a cash buyer who is specifically looking for income property, and even more specifically a vacation rental property,  I firmly believe that there is a value add from having a working STR there.

Like @Collin Hays said, it is being driven more by neighbors tired of poor STR owners not keeping things sorted.We only look for places in vacation areas with a long history of owner driven STRs vs big cities and the like.