One company I reached out to doesn't offer "vacation rental" insurance, but quoted me for an annual tenant at $850/yr and a minimum 30 days (max 3 times a year) tenant for $1,730/yr.

Assuming that the figures and research are correct, if the rent control was in effect for this year, something like 40-50% of rentals in the Bay Area wouldn't keep up with the annual increase cap (based on fair market value). 

There is an upfront mortgage insurance as well as an annual mortgage insurance and the mortgage insurance stays on for the life of the loan. 

The property taxes ($487 annually) were not accurate as you thought.

I currently work for a Fortune 50 company, and I am ready to break free from the rat race and 3% annual "merit increases". 

Also what does Lamar Billboard company typically pay annually for 4 billboards that are lighted and on a single pole to the property owner?

This may result in taxable income on an annual basis.

-We work full time, total salary of about 280k cumulative before taxes annually, and can put down approximately 75K+ on a property currently. 

I believe you will need to average an annual return of around 71% for three years. 

@Henry Wolfe.