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.

What percent of jobs would need to be replaced/automated by artificial intelligence before we began to realize the economy isn't as strong as you think.Thanks again for all that have replied, feel free to leave your comments below!

We want to build trains when automated driving technology is ramping up and will be common before the end of the decade.

Automated appraisal.

Tech is in almost everything and jobs are rapidly being automated this is a STEM area with Drone companies and BioScience for sure, We do have to reinvent ourselves every 4 years to stay current in tech but online Colleges like Nextgenu.com and 100s of other courses are all free online now.

Until these are automated, these jobs will have to be manned by people, who need a place to live.