@Kevin Michel I'd work backwards from your skillset, amount of capital you have (or can raise), and the market you're interested in. 

Market OverviewThe Los Angeles office market is comprised of 210.4 million square feet in twenty-one geographic concentrations ranging in size from the 38.9 million square foot Downtown submarket to the Mid-Cities submarket, which accounts for 1.8 million square feet.

Using a contractor contact the rough estimate of work required is 20-25K.   

Nothing wrong with his opinion, ours is just different.You should consider both and figure out what works for YOU!

We are currently working on a project down there at Mahogany Bay.

Having one left brain and one right brain host was a recipe that worked well for me since 2011. 

I have had success, flipping, BRRRR'ing and house hacking in all these towns so any strategy could work.

Will this only work for a conventional loan?

We worked with a local realtor, and fell in love with this place.

I am not expecting things to work out as you implied but prepare a good exit plan.