These properties are generally in high demand, but on a positive there will be drastically less new inventory of competing rental properties. 

If you need to get it rented fast, a great property manager would list the home for $2100 (below market) and get several quality applicants competing against each other to drive the price up to the max so you don't risk vacancy by starting out too high and gradually reducing to find the sweet spot.

From there, it requires the ability to conduct underwriting the highest and best use of a planned project, which requires a pro forma built by the user or acquired from a competent 3rd party. 

This puts the current market rents of $885–$925 per unit well within the affordable range, with room for modest increases post-renovation.I’ve also reviewed competing properties in the area; apartments seem to be listed between 975 -1000, and houses are listed between 1300-1900.

I drop them and use a competent local RE agent, who did a great job.   

Meet the players. 

What was their level of speed & competence? 

Do you have a CLUE how many big players still make a fortune wholesaling?

Lahaina is a year and a half into recovery with roughly 1500 homes destroyed, The US Army Corps of Engineers and FEMA just competed debris removal.

Many players will not have your best interests at heart.