This is a great place to learn and to connect with people so take advantage of all the great resources.

For some people this is OK since they will get use, future appreciation and a likely refinance in a few years. 

Any advice on the kinds of people I should have in "my team" to make this a success?

I would just say that recently in my experience diversifying out from STR into motels/boutique hospitality has been high risk and set some people off path - it can be a very lucrative and good move - however, if you are having a lot of Success with traditional STR - it seems like a lot of people are looking back and saying they wished they stuck with that and expanded with what was already working!

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.

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.

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