My heart would like to let him stay for free but I doubt I can afford it and also, I’d like to make sure my interests and his are adequately protected in case this get “squirrelly” in any way.

Trail each purchase w a 10% downside stop loss limit order if you're not confident in the REIT, then continue your research on private real estate, and when you have the capital/team in place/knowledge of the local real estate market put it to work then, no rush. 

If at the very least it pays for itself, I see upside equity potential and/ or resale value there.... and a place to stay in Miami.

That means that pets are likely staying at your rental, regardless of whether or not you allow them. 

They will allow tenants to stay without paying full rent and your properties will get trashed.2) Thieves who will lie, cheat and steal from you.

Yes  buyvsome nice rugs that stay down on the corners .Ask upstairs tenants to be quiet.Ask upstairs ti see if rugs and talk helped. 

I started in the land business so I do have a lot of background knowledge at it.I have also been trying to buy a longer term cash flow asset and with rates were they are and cap rates out our way ( at least asking) at 4 to 5 to 6  they still dont make sense. but we are starting to see some 7s so if we can offer and get 8 on a nice project I hope to pull the trigger this year.

How yo gain knowledge to idetify the class of property  

They can advise you on the specific rules and regulations that apply to your situation and help you maximize your deductions while staying compliant with tax laws.

Stay on it or your day in court is coming.