If the business sells (it’s currently listed), the rent payments would stop, but I’d still own the property as an asset.

Where are your fixed rate notes at and their respective monthly PITIA payments ?

Your payments are known. 

Make that rent payment out to you and pick up a roommate.

With $250k in cash, you can easily do down payments on 5-6 rental properties here. 

One has no mortgage, their other has a HELOC for around $20k remaining and is coming to its 10year term that was established before placing with LLC.My predicament is how/best way to pull equity out of either property for a down payment for the 3 family that is valued around $450k.

All told, cash flow will be a function of your down payment and your management of the property.FL tourism continues to flourish. 

Treat this property as a business and factor in all the associated expenses, including mortgage payments (if you pull a loan), maintenance, and potential vacancy periods.To simplify management and make this less of a hands-on job, I’d strongly recommend working with a property management company.

This reduces your housing payment and helps you build equity. 

Does your mortgage include your property tax payments?