Oftentimes my initial consultation call with a potential client runs 1 hr and that still doesn't give me enough time to cover everything about the STR market on O'ahu.  1.  

  $36k - $16k = $20k or $1,600 per month net income left to cover all other expenses...same as above.Median household income in the US is over $80k or more than double these two zip codes.

Do you need to increase rents in the next year to cover your costs?

We have done it both ways where we fund purchase and they cover rehab but if the individual is less experienced we do not do it that way, we have them put more money into the deal from the start and fund the draws, reason why is we also had a deal where the person said they would do this and never did anything and property sat and loan matured and it was a pain.Just recognize you will still not get 100% financing for the purchase, so you are putting money in up front. 

It's amazing what you find covered up in these properties.

The 2 units that are rented are covering the mortgage so yes there's room to lower the price on the other 2.

They have to go overkill crazy like this in order to cover their butts.....Once again, this advice is worth exactly what you paid for it.....

From what I’ve read in The Economist, short-term construction loans or hard money financing could be a great fit to cover the $90K needed.

Before you close, can the rent from your buddy and the midterm tenant cover your mortgage, taxes, insurance, plus a bit extra?

I personally used a 40k ADU grant with CALFHA HPP Cares that covered a chunk of the cost.