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

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.  

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

Are the renters or the landlord expected to cover rent during the evacuation?

Obviously the HOA is keeping values in this neighborhood down because an owner would have a mortgage plus another $715/mo for the HOA, which only covers use to a community center but nothing else.Besides holding costs, is there anything else I should be concerned with for a flip on a land lease? 

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.....

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

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. 

They cover west wood and other west side areas but there are certain places they said they would not cover such as college hill.

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.