I'm a licensed sales person in the state of Florida (located closer to central FL, Space Coast area if you are familiar), with intent to enter the commercial real estate brokerage industry as soon as I can find footing.

As for buy and hold, getting your foot in the door with a house hack is almost always what I recommend. 

Should I use a co-host just to get off the ground on a good foot and rack up some solid 5 star ratings, then transition to self sufficient down the road?   

DR Horton in our market built 2000 sq ft homes in rural areas and smaller homes at 1500 and the only ones they made money on were 1500. they sold the ones above 2000 sq ft at losses or break even close to $150 per square foot. 

Most of the designers I have have sort of a baseline price i.e $2.50/per foot but it can go up or down on other factors

Trust me, by starting off on the right foot, you'll save yourself a lot of headaches down the road!

My thinking immediately turned to researching local rental costs per square foot to determine income potential with triple the current square footage.

Definitely a strong location with great visibility and high foot traffic.Since it’s a NNN,  your expenses are minimal, but if LazyDog ever exits, buildout costs will depend on lease terms and the next tenant.

The cash flow from the properties I am looking @ are low..The buildings are all under performing on what they could potentially get for rent..I see a lot of room for growth and cash flow on these properties, especially with two major projects in the village getting ready to be completed -more jobs and more foot traffic to Main Street are on the way..Carbon copy of Hudson and early 2000’s... Advice, buying a building that wouldn’t maximize for 15 to 24 months ??

You most certainly are starting on the right foot, and have reachable goals set.