I'm trying to learn to evaluate a deal by playing around with numbers with bunch of properties. 

With no mortgage, you should not have paid doc stamps - it's a title play not a sale.Then the Quit Claim:  it costs $10 to file the one page document; an attorney would charge $250 to complete or you can do it yourself by downloading the form.Titling. 

As some of the other commentators have mentioned you have to know your market and while all of Hawaii has a high cost for entry there are still opportunities to be found.I found a very specific market (C-, 2/1 condos, near major hospitals, pet friendly, low HOA) that I studied intensely and because of that specific focus knew a good deal when I saw it and could quickly get the ball rolling while others were still analyzing.Kauai is such a unique community that you will be faced with nuanced challenges but that also means you may find opportunities where others miss them if you know the market.Kauai is the most beautiful island in the state and has a great sense of community, if you want to move there do it and make real estate work for you, don't go about it the other way or you may be left with more properties but also more regret.

Also be aware that reviews and listing quality plays a major role in how much you can charge for a property.

@Jerry Puckett I think (that can be dangerous) that the OP is buying this wholesale, not wholesaling the deal.If this is something you want to manage on your home then I would simply play it by ear. 

Secondarily, outdoor experiences is a must, high bedroom counts (work from home situations), and quiet areas for kids to play in the street (such as a cul de sac).

Typically when I'm advising my clients on submitting an offer, days on market plays a big role on where we come in on price.

Do you have the cash to make those repairs and then sell as more of a retail play?

Maybe the formality and intensity with which you treat this issue will force him to stop smoking it. 

At the end of the day, you are playing odds.