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

So often I see people with all this money and success, but their health is deteriorating.

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

If you really want to sell to people from San Diego then I would just recommend you get your real estate license in whatever state you plan on selling real estate out of.

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

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

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

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.  

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.

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