I may be able to get the Florida home to 1500/mo or so if I rent it as an Airbnb (currently mo to mo $3,300, has a fenced pool, 7 min from the beach), and I’m emotionally tied to the Florida home as I bought the home for my mother who sadly passed away in it from cancer last year.

I quickly started watching his radio shows and eventually got pulled into attending this "strategy session" on the "rich dad world" website (again, can't beleive I fell for something this stupid... literally shameful..) that ended up being emotional and psychological manipulation to get you to buy his course on something I didnt need, but became convinced I absolutely needed and would change my life.

Dealing with serious health issues in the family is a mental, emotional, physical, and financial strain. 

Don't  get emotional about real estate.

There's no emotional "falling in love" with a property like there is with a personal residence that might entice a Buyer to overpay. 

Keeps a bit of emotional separation there if you don't have a PM

This is one of the most unfortunate things as a lot of Mom-and-Pop investors get very invested emotionally in long term tenants and don't feel it is "fair".

Sales is emotional, and you need to create excitement without creating unrealistic expectations.

Fear is a very powerful emotion that wears many different masks and often leads to aggressive, sometimes irrational and anti-social behavior.You mentioned empathy and said...- "What if I knocked on your door during dinner or showed up to your work in the middle of the day in order to sell you something?

So this is not a financial decision as much as an emotional one.