However, there is no specific holding period contained in the tax code or regulations and there is no "safe harbor." 

So if you have the property for a total of 10 years, moved in at year 8, little value or tax advantage.

The risk is not including due diligence caveats in your offer, like inspections.   

Anyway, please feel free to do your own due diligence but it looks like we all got got.

I do intend to stay close to home - but home provides only annual opportunities and I’m looking for year round possibilities with tax deed properties. 

Hawaiian real estate law differs from other western states significantly, mostly due to its monarchal heritage and the Bishop Trust influence.The basics are the same as would be in California; determine the condition of title ownership (individual(s), estate (including conservatorship, if appropriate) OR fiduciary acting for trust.Use a qualified private money equity lender to make a loan sufficient to buy out the cash-only beneficiaryThe legal community in HI and Big Island in particular is small.

Taxes are private, 1099 are private.  

Repairs made while the property is your primary residence are not deductible, but improvements can increase your cost basis, reducing future capital gains tax when you sell.

Quote from @Vikas Jain: Yes, I have already seen the buy-in, im less concerned about that part of it, but just want to make sure its legitimate (plenty of opportunities where buyin is high but it doesn't always mean the product is good, just been burned in the past by others so trying to do better due diligence this time around)Their success rate, as of now, is 100 percent.

Keeping clean records from day one really helps when tax season rolls around.