Downside is you need to do this for every owner and they usually have to sign the bank docs in person.

Only down side, less income.

Honestly that many homes and long distance management, I'd start selling some of them off starting with the ones that are the biggest problem. 

What are some of the biggest misconceptions about 1031 and what are key points I should bring up?

Mostly I want to know other downsides to commission based off sqft rather than %.

The downside to Hollywood being Airbnb-friendly is that Airbnb investors have flocked there so you have a lot of competition.

I like Columbus Ohio because I see it being one of the biggest metropolitan cities in the next 10-20 years, all signs are pointing here!

One of the biggest STR insurance companies in this area is Fudge Insurance , and they always have had the option for my clients.  

As for the median American in my age group, yes I'm way beyond that and I attribute that success to the following:- Willing to delay gratification on a regular basis- Willing to do jobs no one else wants to do- Willing to work long hours for results (a strong work ethic)- Willing to take calculated but high upside/low downside risks- Willing to allow the "fruits of my labor" to be returned to the business instead of paying for a lavish lifestyle- A strong commitment to these principles by my spouse- A strong run of being healthy enough to work to produce excess profits- The fortuitous grace of being born and growing up in the United States, where opportunities for financial success are everywhere and accessible to anyone- A splash of luck at being in the "right place at the right time"

Lack of risk management is the biggest mistake people make in real estate.