There are a few people that would be wise to reach out to in order to get this information.

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?

Too many investors make the mistake of trying to treat it like a short-term rental, which is a great way to get yourself into a bind.You can keep more than one security deposit in the same bank account, but it should be held separate from any of your own money.You need two accounts: checking and savings.

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!

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

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.

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.