Cory,
I grew up on Oahu but family on maui too. How much are those HOAs? You should take a look at some turn-key investor sites on the mainland (Atlanta/Memphis) to get an idea of how good your cash flow could be. I live in seattle which is not great but a little better than Hawaii (which I would like to own a few rentals for no logical reason).
1. What would you do next (in terms of acquiring rental properties) and how would you go about getting there?
You are off to a good start the last thing you should have done was buy anything you don't need meaning a home that is greater than 350k. Although I don't know the quality 250k in Maui is a steal. Going forward just get as many Fanny Mae conventional loans with the least down/longest terms.
2. Knowing my goal, should my next step even be thinking about rental properties?
Yes. I think wholesaling in Hawaii is harder because of the limited supply and buyers. IMO. I don't wholesal