Mold is an issue in FL and needs to be considered.

This issue also naturally drives up deductibles.  

Turning the management of the rental over to a property manager can relive a lot of these issues.

Debt is rarely a factor in their issue. the ultra wealthy I know  with a few exceptions have very limited debt.. to no debt. 

Good cleaners can restock and alert you of issues.

You can wind up with title issues if you are not careful. 

You may could give them a license to use the land, provide a temporary or revocable easement or otherwise permit the use in some way.

Assessments in NJ are not done on sale, unless it's a new build or a complete renovation where the permits tip them to reassess, so every three years or so they reassess all of the properties and taxes go up most of the time.

I had constant issues with the local government and the taxes were absurd.

The ones who bought 3/4 units in good area $500k+ buildings did great, these ran with no issues, rents increased/appreciated.