Also, understand the laws pertaining to service and emotional support animals and whether you are subject to fair housing laws and required to allow them. https://www.nolo.com/legal-encyclopedia/does-the-federal-fai...4.

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.

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".