If you have specific properties in mind, please send them my way, and I can use the tools at my disposal to analyze them.

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.

This one specifically is already slightly undermarket.

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

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.

Where most wanna be investors lacking capital make their mistake is that they don’t understand that if you lack capital you need extensive knowledge; and that knowledge is NOT obtained from a guru mentorship focused on some specific (often fantasy) technique.  

@Mason Bell I would be more specific to avoid the possibility that the agreement could be avoided or declared unenforceable due to vagueness.

From my personal experience I suggest you take a look at lease options, specifically lease option assignments.