Between them, there are two irrevocable trusts. each has an investment property (plus the property where they currently live).

I've succeeded and transformed lives through hard work and dedication.

I currently live in the East Bay and am trying to understand the feasibility of an owner-move in.

Lots of coastal money hoovering up deals that look like major bargains compared to where they live and/or what they are used to... 

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

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. 

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

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.

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

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