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

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

I plan to access some of the equity in my home, along with cash on hand, to purchase and reno property.  

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.

Would love your feedback on first hand experience working with Norada Real estate: http://www.noradarealestate.com/ ?

That will take a good amount of the process off your hands.

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

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

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

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.