You will find some good feedback based on experience from people who have done it before.

Quote from @Hughston Thackham: People see their equity and start to salivate.

But when I was an agent, learning some basic Python and VBA (Excel) really helped me save time in the process of collecting and analyzing real estate data.I've been working with technology for the last 25 years; sometimes you don't need sexy, you just need a tool that works.It's a sin that, we technologist, fall for often: searching for sexy instead of "this old thing just works" :) Agreed, though in my experience, a lot of real estate professionals are far from the most technical people, so having clean and intuitive software UI is very key... but then again the MLS exists and that to my knowledge still doesn't have a back button... lol

I currently rent to up to 10 people however, most rentals don’t include more than 4-5.

When done improperly, as so many people do, an LLC is just a "security blanket"; it gives you the illusion of safety and little else.

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.  

The issues I ran into was the local market was already flooded with STR's and in order to be profitable you had to stand out with a home that was either near an attraction (ie great view, Garden of the Gods, Downtown, or a College) or the unit had to have amenities (Hot tub, Instagram Wall, Pickle Ball Court) that would place your listing far and above other similar listings.I think you should strongly consider if you more interested in moving away and starting a life somewhere else, or in creating a cash flowing investment to supplement your income? 

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..