A lot of sellers are panicking, thinking the market’s going to crash, but they don’t really understand what’s happening behind the scenes—demand is still strong, people are still moving to Florida, and that creates opportunities.I own 32 properties, and I’m always tracking values—rents, insurance, taxes, all of it.

Most Florida markets will share some dynamics though like taxes and insurance. 

Mgt, Landscape/Snow, tax, insurance, utility then debt service. 

So your super basic P&L may look like: $30,000 Rents-$3,000 insurance expense -$9,000 interest-$3,000 taxes-$8,000 operating expenses-$14,000 depreciation ----------------$7,000 loss on paper for the year  so negative taxable income But remember- $14k of that (depreciation) was something we didn't actually spend money on- so cash in bank at year end would be $7,000. 

Secure liability insurance to protect against lawsuits or property-related claims.

"Good about deductions" sounds a lot like "doesn't make enough money to be a homeowner", so he should keep renting from someone else, and you should do what you're going to do with the money and wisdom you earned.Of course I don't know your son, but I think this is too dicey and you are too close to the situation.  

That (and insurance issues) are two big risks.

The taxes and insurance sound like where we are in St Augustine and NY. 

With an 8% mortgage rate, they would pay more than $650k in interest.One major problem for both buyers and owners beyond mortgage rates is the rising cost of property tax and insurance.

IF you need 100% financing and lets say its $200k deal, the lender will be interest only at $150k at 12% = 1500/mo + taxes. insurance etc.