Make them understand that if they damage the property you will tell section 8 and get them thrown out of the program.

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.

Making a post here to connect with local people in your market is a great way to start!

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

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

that's the most powerful way to start. period.and there is absolutely nothing wrong with saving - most people can't even do that! 

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.  

I also understand there are transactions out there that are too small for the larger check writers and in those cases the smaller check writers are still necessary.

Want to understand why our industry is reviled by most people?

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