When we looked at what his cashflow is currently, and then considered what he would net out of a sale post tax, he decided to keep owning the properties.

The 1031 must be a sale of investment property followed by the purchase of investment property. 

BP has built a great selection, all of them worth reading and that will help you build foundational knowledge.To answer this one: the words from old school investor Dolf De Roos "seldom sell" and you will find a lot of post on BP from people who regret selling properties in the past.

You should 100% have insurance because of the worst case scenarios (what if someone dies and they blame you the property owner), but it's not something you'll want to use frequently. 

If they didn’t understand or realize that what they were investing in was not secured by real property, that’s probably because despite being ACCREDITED they’re NOT SOPHISTICATED.  

Do you have LLCs for your properties?

The same is true with property management.

Instead, they get compensated by Turnkey providers or builders with a marketing fee:“…we as the turnkey property promoter gets compensated by and only by the turnkey provider or builder that we are working with, they are essentially paying a marketing fee,” ( Link ).

@Mitch Davidson I purchased a property recently and closing in May.

I've been running the numbers on different properties using a variety of online calculators for properties that I initially thought looked like there may be potential.