Do you have a step by step list when looking at the potential house?

It's a little remote, however, the community seems to be new and growing and there are other houses and developments going up near by.

Without factoring in tax benefits and principal pay down, you're $1800 ahead of the game by house hacking.

Other risks, the contractor walking off the job, a storm hitting and delaying the project for weeks, someone breaking into the home and stealing stuff (which happened just the other day to a client of mine), a squatter, or drunk driver driving into the house (happened a lot at my old job as a firefighter lol).

Stats can be foundhttps://www.ramaui.com/housing-statisticsOr for all islands herehttps://www.hawaiirealtors.com/resources/housing-trends-2/Your realtor can produce more specific stats on your area of interest.

It may make the most sense to focus on home 1 and then leverage the funds from that sale to complete house number 2 and purchase more projects. 

Plus, we had a family in mind that were looking to rent a house.

. - 2 story house with very small rooms and and 2 steps down, imminently as you enter the front door.- Gated community and in a reasonable HOA. - The home is 2 payments behind and already got a letter from the lender about future foreclose.

My wife is from a country that does not allow lending or loans to acquire housing.

At another property with just the sidewalk I let the tenants take care of it, but the liability of these steep stairs makes it too important for it to be haphazard or me having to scold them to shovel and salt the walk and steps.I know in snowy areas people with houses contract plowing for the winter at a flat rate.