not just monitoring maintenance requests but also having the ability to send out contractors in specific circumstances.

Set yearly goes and break them down by quarterThese are just a few, could get more specific if you want

I've read up on a bunch of posts about insurance for flips but most of the answers were very specific to the individuals situation and I wasn't able to find the info I was looking for.I'm going to be buying my first flip soon and I don't plan on hiring a GC, only subs.

Any specific neighborhoods within the region to look into? 

Do you have specific areas on Kauai or Maui in mind?  

Landlording is a LOW MARGIN business and high taxes or insurance will kill your margins quickly or not even give you any margins on the buy in the first place!

They push you to pay $150 for a ad set up fee so your ads get set up correctly and not suspended specifically and when done all the ads get suspended by google and bing right away. 

With the Duplex now, my understanding is I file as though the rental half is a separate property and cut all expenses in half as a write off to my rental income (property tax, insurance, maintenance, improvements, etc...nothing was done specifically to either unit it was full home external work like garage and railing repairs, painting) as well as depreciating the half of the duplex that is a rental after calculating basis.It all seems very straightforward to me but I know I'd be naive not to have a second set of eyes with a professional given my lack of experience.

Over the past 2-3 months, my buyer clients have been offering anywhere from 2k-10k on homes in the 300-500 range depending on how competitive the specific property is and how strong the other offer terms are.

In our deals, we structure it so that the LP gets a 6-8% pref that is structured as debt so they get paid FIRST and the GP gets paid second if there's money left for the split.Also, we only do deals with project IRR of 30-40% so there's enough margin of safety or cushion for the investors because bad things sometimes happen in any investment.