Personally I'm not a fan of life estates as they can go on for longer than intended and prove to be very personal and emotional - deviating entirely from the business purpose you set out with. 

Doesn't even matter if its a family-family team--emotions can often defy rationality, and when that happens, things go sideways.2) Undercapitalized & Poor leveraging strategy: They didn't raise enough.

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.

Clearly the apparent death of retail, lodging and office sectors as a result of Covid-19 will steer investors into areas of real estate that are not weakened by these type of events, and mobile home parks will rank highly.

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

Do you see a glaring weaken in the strategy as a whole?

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