Basically i'm wanting to learn the process of how to maximize return on this property and apply to the next. 

At this time, 30 day rentals are legally allowed for any property in Kailua (unless the association has stricter rules), and I know some people who do quite well renting their SF homes on a 30 day basis.  

Currently, we have about 60 people on the list, but we will likely grow to 500 next year. 

These forums are a great place to learn and meet people, whether you're just starting out or you're a seasoned investor.

And like to get on SM and ruin people if you can..

Basically useless.

., I planned for around $15,000 in basic repairs up front, with another $5,000 per unit for upgrades when the units turned over.

Meanwhile I see people picking it up within days.What am I doing wrong?

People have been telling me for a while to get on this app because of the types of properties and sellers I work with.

Without it, you're really relying on other people's perceptions.