My fiancée and I recently made our first post here and after gaining some great advice we have refined our goals and our now looking for more specific guidance.

I think Small and Mighty Real Estate Investor is another great starter book, as well.Once you get a feel for which specific investing strategy you're looking for, there are tons of other BP books on specific topics that can help you dive deeper!

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

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.

Here's my question: Do I qualify for a tax deduction considering the substantial loss on the property? 

The impacted also ripped off the bumper of their car.The issue is, they don't have a deposit that I can deduct from (I inherited the tenant from the previous property owner).