Myself I have personally done a few PPMs and funds in my career but am not in the day to day like those two aforementioned.

Here in Florida, you first obtain your RE license and work under a Broker for two years. 

However, I am still very hands-on for my management business, typically logging 80 hours a week between my two jobs.

I'm trying to analyze my first property and not sure how to set it up to run the number using the calculator tools here. 2 of the units are successful Airbnb short term rentals, and the other two units are month to month rentals to existing tenants.

Brandon Turner's two books: The Book on Rental Property Investing and The Book on Managing Rental Properties. 

. - The ultimate house hack, live in the small ADU unit and rent out the two levels of the main house on AirBnb in San Francisco (I would have thought STRs are oversaturated in S.F. but it worked for them and they stay fully booked).

A hole or two (check how many you need.) and some plastic pipe?

Funny how she managed two 10 day plus oversea vacations per year for the past 8 years.  

Are the closing costs on both of these two high?

Time, Quality, or Price- you get two out of the three.