In my experience (personal & w/clients) the wife usually doesn't want to pick up and move too often to stick with a strategy like yours.

Whether your at $0 or $10mm of personal cash to start with.   

Personally, I would not keep a rental that is not expected to cash flow. 

Dave Ramsey has a good saying about how Thanksgiving Dinner is different when you owe money to the other person at the table.

Nothing is ever the tenant's fault and the system always blames the owner/PMC.This is why we record EVERY phone call, save every email and will NOT allow our staff to use personal cell phones for texting.

It's very personal and varies wildly. 

While some strategies may work here, those strategies might not suit you.I don't personally do MTR, STR, co-living, or other nuanced strategies.

Personally if you are looking to grow in real estate going the traditional method/way of getting good properties under agreement with traditional financing will get you to where you want to go faster than trying to find all the needles in a haystack.

I’m not a “people person” so they handle screening.

Great leaders get the most out of other people not by pushing or pulling but through modeling and personalized support.