It's like where I live.

I live on the property with a duplex and little house.

Or in other words, the rent received from house hacking would cover our housing costs (mortgage, property tax, insurance, repairs, utilities).Upon research however Oahu seem to be a high cost and low cap rate area similar to SF where we currently live.

What are your thoughts on a tenant who lives in the property(long term) but does not have an active lease.

living I desert ac units is what we primarily do so when hit with so much on heating wasn't prepared

@Marko BukvaAs long as you be living in 1 of the units as your primary residence, then you can do an FHA 203k.If this property will be a flip or you will not live in it as your primary, then you can do a conventional rehab loan like the Homestyle or the CHOICERenovation. 

Of course, there is an issue of where do you live for that period of time to establish that you 1031'ed into another investment property...I agree with @Michael Plaks, I don't know how you figured that savings...As for "...harder to sell to potential buyers," the 1031 transaction is mostly transparent to them. 

It needs little repair/work as the owner is a contractor and his daughter initially lived in the home, so he's kept it up-to-date.

It has a kegorator.I live out in the country and have a few firearms. 

or How fountain (where i live now) is to the springs?