I buy alot of duplexes How did you find this deal and how did you negotiate it?

Think of the EXTREME example where someone buys a ratty house in a TERRIBLE neighborhood and then GROSSLY over improves it because that is what they know and like themselves.

Just purely looking at numbers property 2 comes out ahead buy a few hundred bucks a month depending on how high it gets bid up.Any advice on this?

As you've already observed, when you buy a $500k property and finance at 50% LTV to rent for $2,800/month, your Cash on cash is abysmal.

I don't think I'll be ready for a couple months yet to buy, but I'm looking for some concrete answers so I know what benchmarks I need to hit in order to move forward in a purchase.

Sharing my experience below - Entered into a contract almost 18 months ago, after buying a piece of land.

And would like to use this benefit to buy the land and build a home on it. 

All I do is buy 2-4 units to split and resale.

Hello Bigger pockets, Today I have a question regarding on how I should move my capital before I look to buy my first property.

On Oahu the bottom line of buying in this type of zone is that you will pay higher property taxes and fees, but you have a lot more confidence that you'll be able to continue to operate your property as an STR for years to come.