It seems like everything can easily be automated.

As I get more I'm planning on assistants and book keepers for when my automation isn't enough.Cap rates on larger multi-families around here are around 7%, cap rates on SFD and Duplexes are near 20%.

These are the predominant factors for automated underwriting for DU and LP (Fannie and Freddie).

After many years writing drive control automation & the ongoing debacle with the array of Windows OS I have been a Mac convert for many years...my favorite is take a pic with your iPhone & it appears on your Mac in Photo's & all the intricate excel spreadsheets I design work fine on the Mac. 

I like what you said about automating the payments and the part about saving on the 'status symbols' and then having more flexibility with the small stuff.

The issue I am worried most about is automation and artificial intelligence.  

AI and automation has taken over all aspects of our life.

I'm working with a person in Canada to help me get each property launched on Airbnb and VRBO and to grow the business to 8-20 properties with automation to reduce the amount of time I spend each day managing the properties.

This year, I am working on automating and delegating so we can take the show on the road to other cities. 

Unless airbnb is totally on top of what is a very automated system, the OP's squatter can easily find a way to get a payment accepted.