Also, before you buy another property you'll want to determine your ideal next property - meaning, will it be a "rent ready" house, a major renovation project, or somewhere in between.

I have a property on the barrier island that I do not want to list on MLS but I am interested in connecting with realtors or investors who typically sell or buy pocket listings and may be interested in this property.

However, our research indicates that many DSCR lenders require Florida properties to be held in an entity.Are there any DSCR lenders that offer loans for properties held in a personal name?

If you are going to have property management, that is usually 8-10% off your monthly rent on the property.  

Hey, we can't forget about the folks living in those properties!

Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?

This is required for most landlords in the city, as part of the rental property registration program.

You must have the intent to hold the relinquished property and the replacement property for rental, investment or business use. 

And using the process buy a new property or properties that you also intend to hold for investment use.The issue for you might be that you purchased this property with the primary intent of selling. 

Transferring mortgaged properties to an LLC may trigger due-on-sale clauses, but transferring to a trust first can mitigate this risk.