My family of 6 live and own in a ranch style 3br/2.5ba house with completed bonus room upstairs in a HOA neighboorhood.

You need an accountant and tax consultant and a real estate expert to sit down and put the houses in order of their value vs. their cash flow if you and your mom do not plan to go back to regular jobs.

When I buy one of the deals for my own portfolio, or to rehab the house, I simply pay the agent a commission for finding me a deal (I'm a Broker and they're all licensed reps).

I have four SFH's on Long Island and I have had very good success with section 8 with these houses. 

Given what you described (house hacking, FHA loan) a license will have little affect on your success in the first few years.

The best cities I've done it in are actually the more expensive one's because there's more willing of a seller to let me buy deep(as they're likely owning the house mortgage free) and every fix I do makes more than a 1x on it simply cause of the neighborhood.

Would you ever consider doing a house hack?

Do you want to be a house flipper?

The house is in pristine condition with a top-notch kitchen I added in 2021, and it is located in a premier gated community northeast of Orlando.

For example, I just blew insulation into the dividing wall of a side by side 2 unit house.