Aloha @Robert Silvernagel,
I own and manage vacation rentals in Kihei and have had no problem renting 2 bedrooms units as long as they have 2 bathrooms as well. I agree with @Patrick Franta and @Mike Neubauer that a 1 bedroom will give you a better ROI though because you can still find relatively decent deals on 1 BRs compared to 2 Brs.
As far as the 14.41% in TAT&GET taxes, Mike is right that guests do not like you requesting the additional tax separately so it is better to roll it into the price. This is the primary reason I prefer VRBO over Airbnb. VRBO collects the tax for you as a separate line item on top of your rate. Guests on VRBO never question this because everyone on VRBO does it.
And I think @Alanna Schroeder advice is definitely something most off island owners don't think about. You are going to pay much more for any type of work done (not including all the headaches associated with it) so in my opinion it's better to buy something that's already turnkey.
I also think that if there is any downturn, entry level vacation rentals in places like Kihei will feel it much less than high end luxury vacation rentals and hotels. People will still want to go on vacation but they will just budget a little tighter. At the very worst case, as Alanna mentioned you could convert it to a LTR. There is a huge shortage of long term housing on Maui and rents are definitely not going down so at worst case you would still have this option.