I've outsourced as much as possible over the past 6 months, preferably to folks that I don't have to teach.

Don't depend on one thing.As an agent & investor, when analyzing properties locally: I will look at Airdna (Or one of the many other zestimate style websites)  for a baseline number, correlate that to any rental projections as well as actual rental data that is in the MLS. 

They are free and caterted to teaching and networking in regards to real estate investing!

If you like to pay 5%, I'll teach you for half of that.

We moved from San Diego, CA to San Antonio over 1.5 years ago, but I really do miss the beach and CA and/or FL life style!

Has anyone successfully bought multiple Airbnb-style properties using other people's money to include the down payment?

Such an open ended question:1) learn how to run comps2) learn how to estimate repairs3) learn how to estimate market rents4) learn the styles different investors use to buy (such as 70% rule, 1% rule, etc.)Once you have these 4 down you can determine what prices are investor friendly.Next, you need to sell the home.

Much like what your dad did for you, I’ve started teaching my one and only son to buy real estate and own a business rather than working for someone else.

It would be great to already have a property that I could sell in order to finance other deals, or to focus on flips of any style of home, but I need a place to live and to get out of renting.

I understand the question is wildly off-topic, but I am not sure such a game exists, and I think it would be a great teaching aid for high school students to learn the industry.