We could potentially get a national franchise restaurant or a notable restaurateur looking for a second or third location as a tenant in this space.

@Steve R.Where is the land located? 

Highly desirable location, school district, is a "coveted location" by locals because most of the land is developed and it sits off an extremely accessible roadOur current rent: $2,500 + Utilities (the home could almost certainly rent for $3k).

I am familiar with several real estate markets, so as soon as a property becomes available in a particular location for a certain price, I crunch the numbers and then make a decision.   

I suggest contacting two or three local property manager's to help assess the marketplace, location and get their opinion on rents.

To clarify, the triplex is located on Kauai?

You can use a 1031 multiple times over multiple years to change number, location, price, and type of properties. 

I would highly recommend Astro Property Management located in downtown Huntsville.

You have 100k and the objective of your move is to start in a location which can build passive income short term (within 5 years), not just long term wealth investments. 

As far as the concept of coaching goes, the location of the program is irrelevant.