Is buying a rental into a living trust a good idea?

That seem like a very low for a furnished rental.   

Quote from @Jonathan Blanco: Is it worth seeking lenders with $0 lender fees (such as origination, processing and underwriting fees) or do they just get that money by increasing rates and charging higher points?

Thats why we dont charge by hour for snow , its by the push , or by the inch . 

Quote from @Brandon Vukelich:If you buy a vacation rental in Hawaii, then you're tied to that location.

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

Start by researching local regulations and working with an agent experienced in vacation rentals.

They also have a home vacancy tax in a lot of areas which applies to short term rentals. 

I recommend getting a few quotes and choosing one that is right for your financing strategy. if you are trying to get fix and flip money there is a wide disparity in rates and charges.

We want to get a few rentals up and running and then (if all works well) begin bringing other friends/investors in to invest with us.