Not that it helps you with your current situation but that's just one of the benefits of having an independent agent handle your policies. 

I have been audited by the commission (the result was minimal issues to address) and it is no fun.

As I expand my portfolio, my focus will be on diversifying investments, optimizing property management, and leveraging refinancing options to maximize returns.My long-term vision includes stabilizing my portfolio, achieving financial independence through passive income, and strategically planning for growth and exit strategies.

So would you say that living independently was very transformative and a critical step in becoming the investor you are today? 

It might be a good time to shop the coverage with several independent agents

One last thing that I forgot to mention, which I'm afraid will come to bite me in the *** and cause an audit is that when I sold the home, the closing agent had me sign something that clearly pertained to the qualifications of Section 121 (owned and resided for more than 2 of the past 5 years prior to sale), which I checked all the appropriate boxes that qualified me.... yet there was ONE box, that likely used the phrase, "Did you use any PORTION of the property for business or rental usage during the past 5 years?" 

In Florida, can a newly licensed RE agent (not a Realtor and not yet working for a broker)  join  MLS independently  or do they have to join a local board or  the NAR first?

You should speak to a professional to get such solid advice for your individual circumstance.Now, doing a sale to yourself, even if it is technically not "yourself",  is not an arm's length transaction and the IRS would likely disallow it if audited.

Overall, going with an independent insurance agent will mean they will shop for the best price available… whereas if you called a singular insurer… say Progressive or whomever….

If your "property management company" has a different ownership than the properties it manages, then the property management company must have a licensed broker (independent or employing) running the operations.