He was happy to allow me to rent out nightly because it actually helps keep his property in better shape than a long term renter (having a cleaner in there every turnover, short stay guests always let you know when something isn't working, etc) but didn't want to hassle with worrying about a percentage of income/management, etc.

I know I would be paying a little higher price for the convenience and (truly passive) investments.  

Having lived there a year it is a foreign country and many things are different and culture etc plus you have the native peoples that own huge amounts of real estate and They dont pay income tax and they get food and gas for way cheaper etc etc..

Sounds like you have your act together with passive income and a savings, as well as motivation to build wealth from there.

And some of them are structured in ways where they produce passive income. 

As a short term rental owner I can tell you they are not passive and can be a headache.

Assume my marginal income tax bracket is very high, and mortgage rate is 5.25%.

Moving out of a state with income tax to a state without before selling, saving 10% or more in taxes. 

Then, put together another list for the property called income/expenses.Alternatively, I have another idea that may work.

Your cleaner's income has no bearing on yours.