So Davenport, Celebration, Kissimmee, Champions Gate are all great areas close to Disney with Neighborhoods zoned for STR.

Is this possible in the Bay Area or am I way out of my league?

If you have the greatest mentor and coach at baseball in the world but you don't know anything about the sport then you will be taking that mentor/coaches time to first teach you the basics that you could have easily learned on your own or by watching some baseball games or joining a local league; and that is probably not the the best use of the mentor/coach's time.  

Or how much and what kind of sunblock the big leagues are going to allow on pitcher's forearms in day games next year.

Beat Detroit and National League!

I'm trying to think of the best exit strategy for two properties that are out of my league as a buy and hold investor.

My parents wanted to pay for an expensive Ivy League education.

When I bought my property, one unit had what would become the National champion golf team.

You are way out of your league even dreaming about jumping from ONE single-family-residence to FOURTEEN buildings and TWENTY-EIGHT units <insert various configurations to make those numbers here>?

I only ask that you dont reply saying this is out of your league because I know i can make this work.